Category: chlorides-buliding-blocks

Reference of 2401-24-3, These common heterocyclic compound, 2401-24-3, name is 2-Chloro-5-methoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 113 4-(2-Chloro-5-methoxyanilino)-2,6-di(2-pyridinyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2,6-di(2-pyridinyl)pyrimidine (25 mg, 0.093 mmol) and 2-chloro-5-methoxyaniline (27 mg, 0.140 mmol) similar to Example 111 and isolated as a white solid (20 mg, 55%). 1H NMR (CDCl3): 8.87-8.82 (m, 1H), 8.72-8.64 (m, 3H), 8.08 (d, J=2.7 Hz, 1H), 7.92 (s, 1H), 7.90-7.86 (m, 2H), 7.45-7.38 (m, 3H), 7.33 (d, J=8.7 Hz, 1H), 6.67 (dd, J=3.0, 9.0 Hz, 1H), 3.91 (s, 3H).

The synthetic route of 2401-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 51419-59-1, The chemical industry reduces the impact on the environment during synthesis 51419-59-1, name is p-Tolylmethanesulfonyl chloride, I believe this compound will play a more active role in future production and life.

Ethyl (2E)-3-(2-fluoro-5-nitrophenyl)acrylate (1000 mg, 4.18 mmol) and 1,1?-bi(cyclopropyl)-l-amine (508 mg, 3.80 mmol) were dissolved under argon in abs. N,N-dimethylformamide (10 mE), and then N,N-diisopropylethylamine (1.32 mE, 7.60 mmol) was added. The resulting reaction mixture was stirred at a temperature of 50 C. for a total of 16 h and, afier cooling to room temperature, water and ethyl acetate were added. The aqueous phase was then extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), ethyl (2E)-3-{2-[ 1, 1?-bi(cyclopro- pyl)- 1 -ylamino]-5-nitrophenyl}acrylate (570 mg, 43% of theory) was isolated as a colorless solid, ?H-NMR (400 MHz, CDC13 oe, ppm) 8.27 (d, 1H), 8.16 (m, 1H), 7.63 (d, 1H), 7.18 (d, 1H), 6.46 (d, 1H), 5.19 (br. s, 1H, NH), 4.29 (q, 2H), 1.35 (t, 3H), 1.33-1.27 (m, 1H), 0.78 (m, 4H), 0.49 (m, 2H), 0.18 (m, 2H). Ethyl (2E)-3-{2-[i,i?-bi(cyclopro- pyl)- 1 -ylamino]-5-nitrophenyl}acrylate (570 mg, 1.80 mmol) was then dissolved in abs. ethanol (10 mE), and (Ph3P)3RhC1 (167 mg, 0.18 mmol) was added. After stirring at room temperature for 5 mm, hydrogen was introduced into the reaction solution with a constant gas flow via a gas introduction apparatus for about 9 h. The progress of the reaction was monitored by EC-MS. On completion of conversion, the reaction solution was concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), it was possible to isolate ethyl 3-{2-[1,1?-bi(cyclopro- pyl)- 1 -ylamino]-5-nitrophenyl}propanoate (200 mg, 35% of theory) as a colorless solid, ?H-NMR (400 MHz, CDC13 oe, ppm) 8.07 (m, 1H), 7.94 (d, 1H), 7.11 (d, 1H), 5.40 (bt 5, 1H, NH), 4.18 (q, 2H), 2.77 (m, 2H), 2.64 (m, 2H), 1.30-1.24 (m, 4H), 0.76 (m, 4H), 0.46 (m, 2H), 0.17 (m, 2H). Ethyl 3-{2-[ 1, 1?-bi(cyclopropyl)- 1 -ylamino]-5-nitrophenyl}propanoate (200 mg, 0.63 mmol) was dissolved in abs. tetrahydroffiran (8 mE) and added dropwise to a suspension, cooled down to 0 C., of sodium hydride (38 mg, 0.94 mmol, 60% suspension in oil) in abs. tetrahydrothran (5 mE) under argon. The resulting reaction mixture was stirred at 0 C. for 1 h, and then water was added cautiously, followed by ethyl acetate afier stirring for 5 mm. The aqueous phase was then extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), 1 -[1, 1?-bi(cyclopropyl)- 1 -yl] -6-nitro-3,4-dihydroquinolin-2 (1H)-one (90 mg, 53%) was isolated as a colorless solid, ?H-NMR (400 MHz, CDC13 oe, ppm) 8.16 (m, 1H), 8.04 (m, 1H), 7.53 (d, 1H), 2.93 (m, 2H), 2.78-2.58 (m, 2H), 1.44 (m, 1H), 1.23 (m, 1H), 1.03 (m, 1H), 0.91-0.82 (m, 2H),0.60-0.45 (m, 3H), 0.28 (m, 1H). In the next step, 1-[1,1?- bi(cyclopropyl)-1 -yl] -6-nitro-3,4-dihydroquinolin-2(1H)-one (90 mg, 0.33 mmol) was added together with tin(II) chloride dihydrate (298 mg, 1.32 mmol) to abs. ethanol (5 mE) and the mixture was stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By colunm chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), 6-amino-i -[1,1 ?-bi(cyclopropyl)- 1 -yl]-3,4-dihydroquinolin-2(1H)-one (70 mg, 87% of theory) was isolated as a highly viscous foam, ?H-NMR (400 MHz, CDC13 oe, ppm) 7.18 (m, 1H), 6.58 (m, 1H), 6.48 (d, 1H), 2.78 (m, 2H), 2.59 (m, 2H), 1.47 (m, 1H), 1.08 (m, 1H), 0.98 (m, 1H), 0.90-0.81 (m, 2H), 0.60-0.43 (m, 3H),0.28 (m, 1H). 6-Amino-i -[1 ,i?-bi(cyclopropyl)-i -yl]-3,4-di- hydroquinolin-2(1H)-one (70 mg, 0.29 mmol) was dissolved together with (4-methylphenyl)methanesulfonyl chloride (65 mg, 0.32 mmol) in abs. acetonitrile (5 mE) in a baked- out round-bottom flask under argon, then pyridine (0.05 mE, 0.58 mmol) was added and the mixture was stirred at room temperature for 8 h. The reaction mixture was then concentrated under reduced pressure, the remaining residue was admixed with dil. HC1 and dichloromethane, and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By colunm chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), N-{ 1 -[1,1 ?-bi(cyclopropyl)-i -yl]-2-oxo-i ,2,3,4-tetrahydroquinolin-6-yl}-i -(4-methylphenyl)methanesulfonamide (32 mg, 27% oftheory) was isolated as …

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, p-Tolylmethanesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, JENS; BOJACK, GUIDO; HELMKE, HENDRIK; WILLMS, LOTHAR; LEHR, STEFAN; MUELLER, THOMAS; DITTGEN, JAN; SCHMUTZLER, DIRK; BALTZ, RACHEL; BICKERS, UDO; (119 pag.)US2018/20662; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-11-8, name is 2-(4-Chlorophenoxy)aniline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: chlorides-buliding-blocks

Preparation of l-{4-[2-(4-chlorophe?oxy)phenylamino]-piperidin-l-yl}-ethanoneSTX1629 Cj9H21ClN2O2, MW: 344.8572To a solution of 2-(4-chlorophenoxy)phenylamine (200 mg, 0.91 mmol), l-acetyl-4- piperidone (277 mg, 1.96 mmol) and acetic acid (294 mg, 4.9 mmol) in DCE (3 ml) was added sodium triacetoxyborohydride (519 mg, 2.45 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (10 ml) and extraction with ethyl acetate (3 x 10 ml) followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (263.5 mg, EPO 84%). Analytical data as previously reported. HPLC: 98.13% (2.747 min; isocratic, 90% acetonitrile: 10% water at 1 ml/min).

The synthetic route of 2770-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 384-16-7, name is 2-Bromo-1-chloro-3-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2-Bromo-1-chloro-3-(trifluoromethyl)benzene

2-Bromo-1-chloro-3-trifluoromethylbenzene (2.49 g)In tetrahydrofuran (25 mL) at -78 C.,n-Butyllithium (1.58 N hexane solution, 6.10 mL) was added,And the mixture was stirred at the same temperature for 30 minutes.Then, the obtained lithio compoundAt -78 C.,Imidazo [1,5-a] pyridine-3-carboxaldehyde (700 mg) in tetrahydrofuran (25 mL), and the mixture was stirred at -78 C. for 1 hour. Water was added to the reaction solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and then purified by silica gel column chromatography (ethyl acetate / hexane) to obtain the title compound (1.22 g) as a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 384-16-7, its application will become more common.

Reference:
Patent; DAIICHI SANKYO COMPANY LIMITED; NAGAMOCHI, MASATOSHI; KOZAWA, YUJI; INAGAKI, HIROAKI; GOTANDA, KENTOKU; NOGUCHI, TETSUJI; TORIHATA, MUNEFUMI; YOSHINO, TOSHIHARU; ISOBE, TAKASHI; (113 pag.)JP2016/141632; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-4-fluoroaniline

[446] 2-chloro-4-fluoroaniline (1 g, 7 mmol) was added to concentrated sulfuric acid (15 mL) at Q0 C, followed by the addition of guanidine nitrate (875 mg, 7 mmol). The mixture was warmed to it and stirred for 2 h. Subsequently, the mixture was poured onto ice and neutralized with aqueous sodium hydroxide (4N) until the pH was 9. The mixture was diluted with EtOAc and water, the organic phase was isolated and the aqueous phase was extracted with additional EtOAc (2x). The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (0% – 10% EtOAc/heptane) to afford 2-chloro- 4-fluoro-5-nitroaniline (A2) as light brown solid.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; HUANG, Wei-Sheng; LI, Feng; DALGARNO, David, C.; GONG, Yongjin; ISHCHENKO, Alexey, V.; KOHLMANN, Anna; SHAKESPEARE, William, C.; WEST, Angela, V.; XU, Yongjin; YOUNGSAYE, Willmen; ZHANG, Yun; ZHOU, Tianjun; ZHU, Xiaotian; (444 pag.)WO2015/175632; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 729590-57-2, name is 4-(Benzyloxy)-1-bromo-2-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 729590-57-2

Step B; 3-chloro-4-ethylacrylate-benzyloxyphenol; Ethyl acrylate (5.0 mL, 55.5 mmol) is added to a solution of 4-bromo-3- chlorobenzyloxyphenol (2.7 g, 9.08 mmol), palladium acetate (215 mg, 0.96 mmol), P (o- tol) 3 (550 mg, 1.8 mmol) and Et3N (3 mL, 21.5 mmol) in EtCN (100 mL, HPLC grade). The mixture is warmed to 95C and stirred at that temperature overnight (c. a. 16 h). It is allowed to reach r. t. , filtered trough Celite and partitioned between EtOAc and H20. The organic layer is dried, filtered and concentrated, and the resulting crude is flash chromatographed on Si02 (5% EtOAc/hexanes) to afford 1.79 g of the Heck product (62%, white solid).

The synthetic route of 729590-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66136; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 108-37-2,Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Under similar experimental conditions and reagent amounts in 2.2., the mixture was dissolved in 0.02 mL of IL and 1 mL of DMF. The organic phase was passed through silica gel in order to retain the IL and analyzed by GC and the isolated products characterized by 1H NMR, GC-MS, IR, and mp.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-chlorobenzene, its application will become more common.

Reference:
Article; Cardenas, Juan C.; Fadini, Luca; Sierra, Cesar A.; Tetrahedron Letters; vol. 51; 52; (2010); p. 6867 – 6870;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3ClF2O2S

Step 6-Preparation of N-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-3,5-difluorobenzenesulfonamide (58)Into a microwave reaction vessel were combined (3-amino-2,6-difluoro-phenyl)-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (56, 50 mg, 0.16 mmol), 3,5-difluorobenzenesulfonyl chloride (57, 103 mg, 0.49 mmol), pyridine (0.5 mL, 6.1820 mol) and tetrahydrofuran (3.0 mL). The reaction was warmed in the CEM microwave at 300 watts, 130 C. for 10 minutes. The reaction mixture was partitioned between ethyl acetate and brine. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The compound (58) was isolated using column chromatography (silica, hexane:ethyl acetate 70:30) to obtain 36 mg (46%) compound. MS=482.0.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 210532-25-5.

Reference:
Patent; Spevak, Wayne; Cho, Hanna; Ibrahim, Prabha N.; Shi, Shenghua; Mamo, Shumeye; Gillette, Samuel J.; Zhu, Hongyao; US2008/167338; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 108-37-2,Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation of 2-bromo-6-chlorobenzaldehyde (i-5b). To a solution of l-bromo-3-chlorobenzene (i-5a) (5 g, 26. mmol) in THF (50 mL) was added LDA (1 M, 31.3 mL, 8.7 mmol) dropwise via an addition funnel at -70 C. The mixture was stirred at -70 C for 1 h. DMF (2.87 mL, 39.1 mmol, 227 mmol) in THF (20 mL) was added dropwise maintaining the internal temperature below -70 C. The reaction was stirred vigorously at -70 C for 1 h. Warmed to -30 C, the reaction was poured into 1 M HCl (100 mL) partitioned between water (10 mL) and DCM (30 mL). The aqueous layer was extracted with DCM (20 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to afford the title compound (3.6 g, yield: 59 %). LCMS (ESI) calc’d for C7H4BrC10 [M+H]+: 219, found: 219.

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28591; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

To a mixture of tert-butyl (S)-2-amino-4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (149 mg, 344 mumol) and 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (48 mg, 286.40 mumol) in t-AmOH (3 mL) was added 2.0M t-BuONa in THF (286 muL, 572 mumol) and tBuXPhos-Pd-G3 (23 mg, 29 mumol) and the resulting mixture was heated to 100 C. for 15 h. The reaction mixture was cooled to rt and then concentrated in vacuo to give a (S)-tert-butyl 4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino)-2-((7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl) amino) butanoate intermediate, LCMS (ESI+): m/z=566.5 (M+H)+, which was used without further purification. Of the butanoate intermediate, 80 mg, 141 mumol, was taken up in DCM (1 mL) and TFA (400 muL) and the resulting mixture was stirred at rt for 6 h and then concentrated in vacuo. The crude residue was purified by chiral SFC to give a first fraction containing the title compound. LCMS (ESI+): m/z=510.3 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.18 (s, 1H) 7.19 (d, J=7.28 Hz, 1H) 7.08 (d, J=3.53 Hz, 1H) 6.59 (d, J=3.53 Hz, 1H) 6.40 (d, J=7.28 Hz, 1H) 4.61 (t, J=6.17 Hz, 1H) 3.76 (s, 4H) 3.34-3.40 (m, 3H) 3.33 (s, 3H) 3.22-3.29 (m, 1H) 2.99-3.19 (m, 4H) 2.69 (t, J=6.17 Hz, 2H) 2.58 (br s, 2H) 2.32-2.43 (m, 1H) 2.11-2.21 (m, 1H) 1.86 (dt, J=11.52, 6.04 Hz, 2H) 1.74 (br s, 4H) 1.16 (d, J=5.95 Hz, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics