Tag: M.W=200-300

1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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. HPLC of Formula: C6H3BrClF

A solution of 1-bromo-4-chloro-2-fluoro-benzene (59c, 0.415 g, 1.98 mmol), 6 (0.350 g, 1.8 mmol), K2CO3 (0.746 g, 5.4 mmol) and NMP (4 mL) was stirred and heated to 120 C. for 6 h. The reaction mixture was cooled to RT and diluted with H2O (25 mL) and twice extracted with EtOAc. The combined organic extracts were washed sequentially with water (6 times) and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 column chromatography eluting with a EtOAc/hexane (100% to 75% hexane) to afford 116a

The synthetic route of 1996-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239881; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 63624-28-2, 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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of hydrogen chloride gas in dry ethyl acetate (1.5 M,3.0 mL) was added intermediate IM 3 (0.3 g, 0.6 mmol). The reactionmixture was stirred for 4 h at room temperature. The solvent was removedunder reduced pressure to give solid deprotected product.Various substituted-phenyl sulfonyl chlorides were added dropwise in a mixture of deprotected product and triethylamine (0.5 mL) in anhydrousCH2Cl2 (10 mL). After stirring at room temperature overnight, thereaction mixture was concentrated using a rotary evaporator. The crudeproduct was purified by chromatography on silica gel utilized a mixtureof chloroform and acetone (35:1, v/v) as eluent to furnish the desiredproduct.

The chemical industry reduces the impact on the environment during synthesis 2,4-Dimethoxybenzene-1-sulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Lei; Liu, Jun; He, Wenhui; Bao, Youmei; Sheng, Lei; Zou, Chunyang; Hu, Baichun; Ge, Wentao; Liu, Yang; Wang, Jian; Lin, Bin; Li, Yanchun; Ma, Enlong; Bioorganic Chemistry; vol. 84; (2019); p. 239 – 253;,
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. 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

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

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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

A stirred suspension of 3W-6-iodoquinazolin-4-one in toluene (5 vols) is treated with tri-n-butylamine (1.2 equiv.), and then heated to 70-800C. Phosphorous oxychloride (1.1 equiv.) is added and the reaction mixture is then heated to reflux and stirred at this temperature for at least 2 hours. The reaction mixture is then cooled to 55C and toluene (5vol) added followed by 3-chloro-4-{[(3-fluorophenyl)rnethyl]oxy}aniline (1.03 equiv.). The reaction mixture is then warmed to 70-900C and stirred for at least 2 hours. The resultant slurry is transferred to a second vessel. The temperature is adjusted to 70-750C and 8 molar aqueous sodium hydroxide solution (2 vols) added over 1 hour, followed by water (6vol.) maintaining the contents at 70-850C. The mixture is stirred at 70-850C for ca. 1 hour and then cooled to 20-250C. The suspension is stirred for ca. 2 hours and the product collected by filtration, and washed successively with water, 0.1 molar aqueous sodium hydroxide, water, and IMS, then dried in vacuo. EPO

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM [CORK] LIMITED; WO2006/113649; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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. Computed Properties of C6H3BrClN3

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (CAS 13526-66-4, 1.327 g, 5.71 mmol) was dissolved THF (40 mL) and under nitrogen conditions, it was cooled down to 0 0C and ethyl magnesium bromide solution (1 M, 6.85 mL) was added. The RM was stirred at RT for 30 min then a solution of 7-fluoro-quinoline-6-carbaldehyde (Intermediate K, 1.0 g, 5.71 mmol) in THF (20 mL) was added by 0 0C. The RM was stirred at RT for 2 h. The solvent was partially removed by evaporation and water (40 mL) was added to the residual mash. After 1 h stirring, the crystallized product was filtered and dried overnight under vacuum to afford the title compound as a powder (tR 3.70 min (conditions 5), MH+ = 329, 1H-NMR in DMSO-d6: 8.90 (dd, 1H); 8.46 (d, 1H); 8.29 – 8.23 (m, 2H); 7.72 (d, 1H); 7.54 – 7.49 (m, 2H); 7.40 (d, 1 H); 6.56 – 6.49 (m, 2H)).

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; McCARTHY, Clive; SCHOEPFER, Joseph; STUTZ, Stefan; WO2011/15652; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, molecular formula is C6H3BrClF, 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 3-Bromo-4-fluorochlorobenzene

A solution of 2-bromo-4-chloro-1-fluorobenzene (175 .iL, 1.377 mmol) in THF (4.59 mL) at -78 C was treated with n-BuLi (2.6 M, 741 jiL, 1.928 mmol) and the reaction mixture was stirred for 30 mm. To this was added tert-butyl 4- (methoxy(methyl)carbamoyl)piperidine-1-carboxylate (250 mg, 0.918 mmol) in one portion. The cooling bath was removed and the resulting reaction mixture was allowed to warm to rt and stirred for 1.5 h. Purification by automated flash silica gel chromatography using 10% EtOAc in hexanes afforded tert-butyl 4-(5-chloro-2-fluorobenzoyl)piperidine-1-carboxylate (287.9 mg, 92%) as a yellow oil. ESI-MS mlz [M+Na]+ 364.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1996-30-1, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; HITCHCOCK, Stephen; HOPKINS, Maria; KIKUCHI, Shota; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; MACKLIN, Todd; WO2015/123505; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics