Month: February 2021

Related Products of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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.

Step 1: Preparation of Intermediate 3,5-chlorophenyl)hydrazine (I-la) To a cold suspension of 3, 5-dichloroaniline (15.0 g, 92.58 mmol, x 4 batches) in conc. HCI (45 mL, for each batch) was added a solution of NaNO2 (7 g, 101 .44 mmol, for each batch) in water (65 mL, for each batch) at 100C and stirred for 30 minutes. Then a solution of SnCI2 (52.49 g, 277.7 mmol, for each batch) in conc. HCI (45 mL, foreach batch) was added slowly. After addition was complete, a white precipitate was formed which was stored at 4C for 7 h. The precipitated solid was collected by filtration, washed with hexane and suspended in 10% aq NaOH solution (pH = 13) and extracted with Ethyl acetate (4 x 200 mL). The organic layer was washed with water (250 mL), brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Thesolids thus obtained from 4 batches were combined and was washed with n-hexane to afford 45 g (68.6%) of 3,5-chlorophenyl)hydrazine a-ia) as an off-white solid.NMR (400 MHz, DMSO-d6): 66.75 (5, 1 H), 6.72 (5, 2H), 5.30 (br s, 1 H, -NH), 3.58 (br s, 2H, -NH2). ESI MS: m/z 179.0 (M+2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; KONDREDDI, Ravinder Reddy; SMITH, Paul William; WO2014/37900; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 873-38-1, 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. 873-38-1, name is 2-Bromo-4-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-bromo-4-chloroaniline (1 g, 4.84 mmol) in acetic anhydride (5 ml, 4.84 mmol) was stirred at RT for 1.5 hrs. The resulting suspension was collected by filtration and dried on a vacuum line to give the title compound as a white solid. (0532) LC-MS: Rt 0.90 mins; MS m/z 250.0 [M+H]+; Method 2minLowpH (0533) 1H NMR (400 MHz, DMSO-d6) delta 9.51 (1H, s), 7.78 (1H, d), 7.62 (1H, d), 7.44 (1H, dd), 2.08 (3H, s).

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

Reference:
Patent; NOVARTIS AG; EDWARDS, Anne-Marie; AHMED, Mahbub; PULZ, Robert Alexander; ROONEY, Lisa Ann; SMITH, Nichola; TROXLER, Thomas Josef; (31 pag.)US2015/329549; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 157590-59-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 157590-59-5 name is 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1: Synthesis of 4-[6-chloro-5-(trifluoromethyl)-lH-l,3-benzodiazol-2- yl]butan-l-ol [0593] 4-chloro-5-(trifluoromethyl)benzene-l,2-diamine (5.00 g, 23.74 mmol) was dissolved in HC1 solution (4 M solution) (18.85 ml) at r.t. and delta-valerolactone (2.62g,26.12 mmol) was added slowly. The reaction was heated to 135 C for 2 hrs then slowly cooled to r.t. The reaction was quenched by the addition of sat. NaHC03 solution (200 ml) to pH 8. The mixture was extracted with EtOAc (3 x 150 ml) and the combined organic layers were dried over Na2S04, filtered and concentrated in vacuo to give the crude product as a brown solid which was triturated with ether (100 ml) to give the pure product (5.88 g,84%): MS (ESI+) for Ci2Hi2ClF3N20 m/z 293.4 [M+H]+; LC purity 90% (ret. time, 1.49 min); 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.39 – 1.72 (2 H, m), 1.71 – 1.94 (2H, m), 2.87 (2 H, t, 7=7.61 Hz), 3.58 (2 H, t, 7=6.09 Hz), 7.42 – 7.96 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; OLHAVA, Edward James; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; WO2012/75492; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 16793-91-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16793-91-2 name is 2-Chlorophenethyl Bromide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Ethyl 2-piperidin-4-ylacetate 11 (1 g, 5.84 mmol, 1.0 equiv.) and substituted (2-romoethyl)benzene derivatives (12a-b) (7.01 mmol, 1.2 equiv.) were dissolved in 20 mL acetone.Then, anhydrous K2CO3 (11.68 mmol, 2 equiv.) and catalytic amount KI were added. The reactionmixture was refluxed for 4 h. After completion of the reaction, acetone was concentrated, and theresidue was dissolved in water (60 mL) and extracted with ethyl acetate (60 ¡Á 3 mL). The combinedorganic layers were dried over Na2SO4, filtered, and concentrated in vacuum. The obtained oil wasused in further synthesis without purification yielded compounds 13a-b (Yields were 67% and 72%).Then, 4 mol/L KOH (2.5 equiv.) was added to the solution of compounds 13a-b in C2H5OH: H2O =5:1(6 mL). The reaction mixture was stirred at room temperature for 7 h. After completion of the reaction, the reaction mixture was evaporated to dryness after neutralization with dilute hydrochloricacid solution. Poured into ethyl acetate to deposit the solid, after cooling off, the mixture was filteredand washed with cold ethyl acetate to give compounds 14a-d.Finally, intermediates (14a-b) (1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) wereadded to 6 mL DMF and stirred at room temperature for 20 min. Then, intermediates (15a-b) (1.0equiv.) was added and stirred at room temperature for 4 h. After completion of the reaction, thereaction mixture was quenched with saturated NaCl solution. The aqueous phase was extracted withDCM. The DCM layer was combined and washed with brine solution. The organic layer was driedover anhydrous Na2SO4 and the solvent was removed under reduced pressure. After concentration,the crude product was purified by silica gel column chromatograph using a methanol indichloromethane gradient (DCM:methanol = 60:1-5:1) yielded compounds 16a-d.N-(1H-Indol-5-yl)-2-(1-phenethylpiperidin-4-yl)acetamide (16a). 2-(1-Phenethylpiperidin-4-yl) aceticacid (140 mg, 0.57 mmol), 1H-Indol-5-amine (63 mg, 0.48 mmol), PyBOP (295 mg, 0.57 mmol),DIPEA (93 mg, 0.72 mmol), DMF (6 mL). Yellow solid, m.p.: 165-167 C, yield: 80.70%, 1H NMR(400 MHz, CD3OD) delta 7.74 (d, J = 2.0 Hz, 1H), 7.28 (tt, J = 13.1, 6.8 Hz, 6H), 7.20 (d, J = 3.1 Hz, 1H),7.15 (dd, J = 8.6, 2.0 Hz, 1H), 6.37 (d, J = 3.1 Hz, 1H), 3.60 (d, J = 14.9 Hz, 2H), 3.26 (d, J = 5.0 Hz, 1H),3.08-3.01 (m, 3H), 2.39 (d, J = 7.0 Hz, 2H), 2.21-2.13 (m, 1H), 2.04 (d, J = 15.4 Hz, 2H), 1.74-1.60 (m,2H), 1.27 (s, 2H). 13C NMR (151 MHz, CD3OD) delta 170.66, 136.38, 133.81, 129.79, 128.59, 128.42, 127.97,126.86, 125.29, 115.83, 115.76, 112.47, 110.75, 101.07, 72.24, 70.09, 60.80, 57.69, 53.42, 52.37, 41.90,31.68, 31.23, 29.38, 28.89, 22.34, 13.05. HRMS (ESI): calcd. For C23H27N3O [M + H]+ 362.2227, found362.2242.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chlorophenethyl Bromide, and friends who are interested can also refer to it.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, 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. Application In Synthesis of 4-Bromo-3-chlorobenzene-1,2-diamine

Example 13 N2 -[(4-Chloro-lH-benzimidazol-5-yl)methyl]- N4 -(5-cyclopropyl-lH-pyrazol-3-yl)pyrimidine-2,4- diamine (1-3) step 1 : A mixture of 4-bromo-3-chloro-benzene-l,2-diamine (CASRN 1008361-80-5, 27 g, 0.1221 mol) and formic acid (80 mL) was heated to reflux for 1.5 h. After the completion of the reaction, 10% NaOH was added until the solution basic. The resulting solid was filtered and washed well with water then dried over night over suction to afford 22 g (78%) of 5-bromo-4-chloro-lH-benzoimidazole (128) as pale yellow solid which was used without additional purification.

The synthetic route of 4-Bromo-3-chlorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

General procedure: In a round bottom flask under N2, 2-bromo-1-(1H-indol-3-yl)ethanone (1) (500 mg, 2.1 mmol), p-toluenesulfonyl chloride (439 mg, 2.3 mmol), DMAP (26 mg, 0.21 mmol), and triethylamine (0.3 mL, 2.1 mmol) were dissolved in 20 mL of dry CH2Cl2, and the solution was stirred at room temperature until that the starting material had disappeared by checking TLC. The reaction mixture was quenched by dilution with CH2Cl2 (30 mL), and the organic extract was washed with 1 N HCl (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and the solvent was removed under vacuum. The product was purified by silica gel column chromatography using CH2Cl2 to give 379 mg of (2a) as brown crystalline plates.

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vera, Gonzalo; Lagos, Carlos F.; Almendras, Sebastian; Hebel, Dan; Flores, Francisco; Valle-Corvalan, Gissella; Pessoa-Mahana, C. David; Mella-Raipan, Jaime; Montecinos, Rodrigo; Recabarren-Gajardo, Gonzalo; Molecules; vol. 21; 8; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

97329-43-6, name is 1-Bromo-2-chloro-3-methylbenzene, 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. Recommanded Product: 97329-43-6

A mixture of l-bromo-2-chloro-3-methyl-benzene (3.0 g, 14.6 mmol), phenylmethanethiol (2.1 g, 17.5 mmol, 2.0 mL), (lE,4E)-l,5-diphenylpenta-l,4-dien-3- one;palladium (2.6 g, 2.9 mmol), DIEA (5.6 g, 43.8 mmol, 7.6 mL), and (5-diphenylphosphanyl- 9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (1.6 g, 2.9 mmol) in dioxane (60.0 mL) was degassed and purged with 2 for 3 times, and then the mixture was stirred at 100C for 12 h under N2 atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (S1O2) to afford benzyl(2-chloro-3- methylphenyl)sulfane (2.6 g, 53.6% yield) as a yellow solid. 1HNMR (400MHz, CHLOROFORM-^ delta 7.44 – 7.37 (m, 2H), 7.36 – 7.23 (m, 3H), 7.16 – 7.03 (m, 3H), 4.42 – 3.93 (m, 2H), 2.73 – 2.22 (m, 3H).

The synthetic route of 97329-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (214 pag.)WO2019/94641; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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. Product Details of 918538-05-3

69A. Preparation of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine A solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with 3-cyclopropyl-1H-pyrazol-5-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOH and dried under vacuum to afford 69A as a solid (1.3 g, 90%). HPLC tR=3.301 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+=275.37. A solution of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine (1A) (100 mg, 0.36 mmol) and piperidine-4-carboxamide (467 mg, 3.6 mmol) in NMP (1 mL) was heated in a microwave safe tube (CEM Corporation, 10 mL) at 100 C. for 40 minutes using 300 W continuous power. The reaction was diluted with EtOAc (10 mL) and washed with 10% aqueous LiCl solution (2*10 mL). The organic layers were combined and dried (Na2SO4), filtered and concentrated. The crude product was purified by preparative reversed-phase HPLC to afford the title compound (23 mg, 15%). HPLC tR=2.398 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

Step B;. A solution of sodium nitrite (0.63 g, 9.2 mmol) and H2O (1.9 mL) was added dropwise at 0¡ã C. to a solution of 2-bromo-5-chlorobenzenamine (1.6 g, 7.7 mmol) in 12N HCl (18.2 mL) and TFA (2.31 mL). The reaction mixture was stirred at 0¡ã C. for 1 h followed by the dropwise addition of a solution of tin(II)chloride (3.1 g, 16.9 mmol) in 12N HCl (4.6 mL) and H2O (0.6 mL) at 0¡ã C. The reaction mixture stirred for 1 5 h at 20¡ã C. and was filtered and placed under vacuum to give 1 -(2-bromo-5-chlorophenyl)hydrazine hydrochloride (2.0 g, 7.8 mmol).

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/27178; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 75717-77-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 75717-77-0 name is 2,4-Dichlorophenylacetylene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Weighed 2,4-dichlorobenzyl alkyne compound (81.6mg, 0.5mmol) into the round bottom flask; re-weighed compound 3,4-methylenedioxy-benzyl azide (120mg, 0.68mmol, 1.4eq) into round-bottomed flask; dimethyl sulfoxide (0.2mL); amount of tert-butanol solution (4mL) and H2O (2mL) dropped to the mixture; after five co-catalyst weighed water copper sulfate (390mg); and then said take ascorbic acid sodium salt (290mg). The clarification becomes cloudy, yellow. Was stirred for 5 hours at room temperature, after treatment experiment, ice-water was added with stirring (15mL), the reaction was quenched; (30mL ¡Á 3) and extracted with ethyl acetate; the organic phase was washed with H2O (25mL ¡Á 2), saturated chloride sodium solution (30mL ¡Á 2) and washed; with an appropriate amount, and the organic phase was dried over anhydrous sodium sulfate; filtered andAnd concentrated to a solid, brown, purified by column chromatography [the V (dichloromethane) :V (petroleum ether) = 1: 1] to give a white solid 125.0 mg,Yield 75%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichlorophenylacetylene, and friends who are interested can also refer to it.

Reference:
Patent; Changzhou University; Chen, Xi; Liang, Cuirong; Yang, Qinghong; Ren, Jie; Jin, Guihua; Huang, Qianhui; Xu, Yuanyuan; Hu, Kun; (32 pag.)CN105440020; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics