Chlorides-buliding-blocks

2533-69-9, Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2533-69-9.

[00748] To a solution of 4-chloro-5-(4-chlorobenzyloxy)benzene-1,2-diamine (282 mg, 1 mmol) in DCM (4 mL) and ethyl ether (1.6 mL) at 0C was added methyl 2,2,2-trichloroacetimidate (260 mg, 1.5 mmol) and TFA (1.6 mL). The resulting reaction mixture was stirred at 15C for 20 h. The reaction was quenched by adding ice, and white solid was formed, and then filtered. The solid was washed with excess DCM. The filtrate was concentrated in vacuo at 20C to give the residue (200 mg) as a tan gum,. The residue was used directly in the next step. ESI-MS (EI+, m/z):

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; MAHONEY, Sarah; MOLZ, Lisa; NARAYAN, Sridhar; SAIAH, Eddine; (516 pag.)WO2018/191146; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

96558-78-0, These common heterocyclic compound, 96558-78-0, name is 3-Bromo-5-chlorophenylamine, 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.

3-chloro-5-bromoaniline (1 g, 4.84 mmol) was dissolv ed in 75% I LSO ( 10 mL). Then glycerol (1.1 1 g, 12.1 mmol ) and nitrobenzene (0.59 g. 4.84 mmol ) were added. The reaction mixture was stirred at 150C for 3 hours under N2. EtOAc (50 ml ) was added and the mixture was adjusted to pH to 6-7 with a 30% solution of NaOH in water. The solid was filtered off over celite and the organic layer was separated and ev aporated. The residue was purified by flash column chromatograph over silica gel (gradient eiuent: petroleum ether EtOAc from 20/ 1 to 5/1). The desired fractions were collected and the solvent was evaporated to give a mixture of intermediate 457 and intermediate 458 (750 mg) as a white solid.

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 96558-78-0.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 2453-46-5, name is Chlorocycloheptane, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2453-46-5. 2453-46-5

A 1.64 M THF solution of phenylmagnesium chloride (1.10 mL, 2.40 mmol) was added at 0 C. to 0.6 mL of a THF solution of aluminum chloride AlCl3 (80.0 mg, 0.60 mmol). The reaction mixture was stirred at room temperature for 1 hour. To the resulting solution was added 1,2-bis(bis(3,5-di-tert-butylphenyl)phosphino)benzene ([3,5-(t-Bu)2]-DPPBz) (13.4 mg, 0.015 mmol) and a 0.1 M THF solution of iron chloride FeCl3 (0.15 mL, 0.015 mmol) at 0 C., followed by chlorocycloheptane (66.3 mg, 0.5 mmol). The coupling reaction was performed at 80 C. for 24 hours. After cooling to room temperature, a portion of the reaction mixture was taken out, and the yield of the product was measured by gas chromatography (GC), using undecane as an internal standard. The yield was 94%. The results are shown in the Entry 5 column of Table 8.

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 Chlorocycloheptane.

Reference:
Patent; Kyoto University; US2011/152523; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution under N2 of3-bromo-6-chloro-imidazo[1,2-b]pyridazine (1 g, 4.3 mmol) in dioxane (45 mL), Pd[P(C6H5)3]4(0.248 g, 0.2 mmol), 5-indole-5-boronic acid (0.728 g, 4.51 mmol) and Na2CO3(2 M, 7.7 mL) were added. The mixture was stirred for 21 h at 100 C. Thereaction was monitored by TLC. The solvent was evaporated under reducedpressure. The crude residue was diluted and stirred in AcOEt and ammoniumchloride solution (saturated). The product was extracted with AcOEt, and theorganic layer was washed with NaCl solution. The organic layer was dried overNa2SO4, filtered, and evaporated under reduced pressure.The crude residue was purified by chromatography on silica gel using DCM-AcOEt(6:4) afforded 6a in 72% yield(0.840 g) as a light green powder.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

60633-25-2, Name is 2-Bromo-4-chloro-1-methoxybenzene, 60633-25-2, 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.

5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =Cl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77%) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid. This compound was used in the next reaction with no further purification. Methyl (5′-chloro-2′-methoxy-4-nitro-2-biphenyl)carboxylate (structure 39 of Scheme XI, where R1 =H, R2 =Cl)

Statistics shows that 2-Bromo-4-chloro-1-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 60633-25-2.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1 .00 mmol) in THF (5 ml_) was added EtMaBr (1 M in THF, 1 .50 ml_, 1 .50 mmol) at -10 QC. After stirring at -10 QC for 1 h, i -methyl-I H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to rt slowly and stirred for 2 h. The reaction was quenched with saturated NH4CI solution and concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; DAI, Miao; FU, Xingnian; HE, Feng; JIANG, Lei; LI, Yue; LIANG, Fang; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YAN, Xiaoxia; YU, Zhengtian; ZHANG, Ji, Yue; WO2011/20861; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4863-91-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4863-91-6 as follows.

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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.

a) To a stirred suspension of (A7) as obtained from example 5 (60.0 g, 126 mmol) in acetonitrile (180 ml.) was added pyridine (35.6 ml_, 440 mmol) and 2-chloro-6-fluoroaniline (27.4 g, 188 mmol, CAS-no. 363-51-9 obtained from Combiblocks, product code OS-7812; alternatively a preparation of 2-chloro-6-fluoroaniline is described in US 4,089,958, example XVIII) at 22C. The cloudy solution was cooled to 0-5C and phosphoryl chloride (21.2 g, 138 mmol) was added over a period of 10 min. The reaction mixture was stirred for 1 h resulting in a clear solution. Methanol (360 ml.) and 85% phosphoric acid (12.8 ml_, 189 mmol) were added and the mixture was heated to 60C for 2 h. (0796) The reaction solvent was partially removed by distillation (95C bath, 64-72C internal temperature) to give 420 ml. distillate. The distillation residue was slowly cooled to 22C and stirred for 16 h. The resulting suspension was cooled to 0-5C and stirred for additional 2 h. The solid was isolated, washed two times with 2-propanol (30 ml.) and dried in vacuum at 50C for 16 h to give crude product Compound (I) as a white solid (55g, 106 mmol) in 84% yield. (0797) HPLC (method 1 ): Rt = 2.81 min (> 98% area) (0798) b) The reaction product (30.0 g, 57.6 mmol) was further purified by suspension in anhydrous ethanol (450 ml.) and heating to 60C. The resulting clear solution was filtered, the filter cake was washed two times with hot anhydrous ethanol (30 ml.) and the filtrate was concentrated by distillation of solvent (270 ml. distillate) at 100C bath temperature. The solution was cooled to 50C, seeded (I) (0.3 g), and cooled stepwise to 0-5C over 4h. The precipitated solid was isolated, washed two times with anhydrous ethanol (15 ml.) and dried in vacuum at 50C for 16h to give Compound (I) as a white solid (25.7 g, 49.3 mmol) in 86% yield from crude (0799) Compound (I). (0800) HPLC (method 1 ): Rt = 2.81 min (> 99% area) (0801) 1H NMR (400 MHz, DMSO-d6) d ppm 1.29 (t, J=7.15 Hz, 3 H) 1.45 (d, J=6.36 Hz, 3 H) 3.80 (q, J= 7.09 Hz, 2 H) 4.44 – 4.55 (m, 2 H) 5.36 (dt, J=12.78, 6.33 Hz, 1 H) 5.80 (t, J= 5.75 Hz, 1 H) (0802) 7.30 – 7.47 (m, 3 H) 7.50 – 7.66 (m, 2 H) 10.05 (s, 1 H) (0803) LCMS (method 1 ): Rt = 0.90 min; MS (ESIpos): m/z = 521 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 363-51-9, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; GRADL, Stefan, Nikolaus; RUBENBAUER, Philipp; VAN DER HAAS, Henricus, Nicolaas, Sebastian; GIELING, Reinerus, Geradus; (127 pag.)WO2019/197239; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, I believe this compound will play a more active role in future production and life. 15205-15-9

Step 1: (S) -tert-Butyl (1- (4- ( (2-chloro-6-fluorobenzyl) carbamoyl) -2- (3, 4-dimethoxyphenyl) oxazol-5-yl) ethyl) carbamate[0569]To 15 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3, 4-dimethoxyphenyl) oxazole-4-carboxylic acid (0.3 g, 0.764 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (219.65 mg, 1.15 mmol) and 1-hydroxy-7-azabenzotriazole (156.4 mg, 1.15 mmol) . The mixture was stirred at 0 for 30 minutes. To the mixture were added dropwise (2-chloro-6-fluorophenyl) methanamine (0.12 mL, 0.92 mmol) and N, N-diisopropylethylamine (0.4 mL, 2.3 mmol) , and the mixture was stirred at rt for 12 hours. The reaction mixture was washed with water (20 mL ¡Á 3) . The organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 6/1) to give the title compound as a white solid (188 mg, 46) .

The chemical industry reduces the impact on the environment during synthesis 15205-15-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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 66A N-(2-chloro-6-fluorophenyl)-4-ethyl-2-(methylthio)pyrimidine-5-carboxamide Example 28B (15 g, 76 mmol) was dissolved in dioxane (300 mL) and sulfurous dichloride (6.62 ml, 91 mmol). N,N-dimethylformamide (3 drops) were added. The reaction mixture was stirred for 60 minutes at ambient temperature then 2-chloro-6-fluoroaniline (13.22 g, 91 mmol) was added. The reaction mixture was then stirred at 100 C. for 16 hours. The flask was then put into an ice bath and the reaction mixture was quenched by careful addition of saturated aqueous sodium bicarbonate (200 mL). After diluting with 200 mL of ethyl acetate, the reaction mixture was poured into a separatory funnel, the aqueous layer was removed and the organic layer was washed with saturated aqueous sodium bicarbonate (1*150 mL), diluted aqueous sodium bicarbonate (10% wt, 1*150 mL), and saturated aqueous brine (1*150 mL), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco, Redi-Sep column, 5-85% ethyl acetate/hexane, linear gradient) afforded the title compound.

The synthetic route of 363-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Woods, Keith W.; Mastracchio, Anthony; Lai, Chunqiu; Gandhi, Viraj B.; Penning, Thomas D.; US2013/225589; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics