Tag: M.W=200-300

Adding some certain compound to certain chemical reactions, such as: 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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 2770-11-8. 2770-11-8

Preparation of {4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}- cyclopentylmethanone STX1685 C23H27ClN2O2, MW: 398.94To a solution of 2-(4-cUorophenoxy)phenylarnine (100 mg, 0.45 mmol), 1- cyclopentylcarbonyl-4-piperidone (144 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 100C for 15 minutes hi a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) EPO 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 (82 mg, 43%). 1H NMR (300 MHz, CDCl3): delta 1.16-1.36 (2H, m, 2 x CH)3 1.47-1.56 (2H, m, 2 x CH), 1.59-1.78 (6H, m, 6 x CH)5 1.93-2.08 (2H, m, 2 x CH), 2.76-2.87 (2H, m, 2 x CH), 3.07-3.18 (IH, m, CH), 3.43-3.52 (IH, sept, J = 3.9 Hz, CH), 3.78-3.89 (IH, bd, J = 13.8 Hz, CH), 3.97-4.10 (IH, m, CH), 4.31-4.42 (IH, bd, J = 13.5 Hz, NH), 6.55-6.62 (IH, td, J = 1.5, 1.2, 1.2, 7.7 Hz, ArH), 6.68-6.71 (IH, dd, J = 1.5, 8.1 Hz, ArH), 6.73-6.77 (IH, dd, J = 1.5, 8.1 Hz, ArH), 6.79-6.84 (2H, m, ArH), 6.95-7.01 (IH, td, J = 1.5, 0.6, 1.5, 7.7 Hz, ArH), 7.16-7.22 ppm (2H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 19.5, 19.6, 30.2, 32.2, 33.2, 40.6, 44.1, 49.9, 112.2, 117.2, 118.8, 119.6, 125.3, 127.9, 129.8, 138.9, 143.1, 156.1, 175.4 ppm LCMS: M+H: 421.46 HPLC: 98.41% (3.124 rnin, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

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 2-(4-Chlorophenoxy)aniline.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
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54932-72-8, The chemical industry reduces the impact on the environment during synthesis 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

To a solution of 4-bromo-1 -chloro-2-methyl-benzene (30 g, 146 mmol) and benzoyl peroxide (0.71 g, 3 mmol) in acetonitrile (70 mL) was added N-bromosuccinimide (28.6 g, 161 mmol) at 90C and the mixture was stirred overnight. The solution was evaporated under reduced pressure and the crude material was purified onsilica gel to give 4-bromo-2-(bromomethyl)-1 – chloro-benzene as a white solid (40.3 g, 95% yield).

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

Reference:
Patent; BASF SE; WINTER, Christian; RHEINHEIMER, Joachim; WOLF, Antje; POONOTH, Manojkumar; TERTERYAN, Violeta; WIEBE, Christine; KREMZOW-GRAW, Doris; ROeHL, Franz; GRAMMENOS, Wassilios; ROHRER, Sebastian Georgios; WIEJA, Andy; ROSENBAUM, Claudia; WO2014/207052; (2014); A1;,
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The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life. 933190-51-3

A mixture of 8-bromo-6-chloroimidazo[l ,2-b]pyridazine (300 mg, 1.3 mmol), 6-(3- methylcyclopentyl)pyridin-2-amine (277 mg, 1.56 mmol), Pd2(dba)3 (75 mg, 0.13 mmol), BINAP (324 mg, 0.52 mmol), Cs2C03 (1272 mg, 3.9 mmol) and dioxane (20 mL) was heated to 100 C with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200 – 300 mesh, petroleum ether : ethyl acetate = 5 : 1) to give 6-chloro-N-(6-(3-methylpyrrolidin-l-yl)pyridin-2-yl)imidazo[l ,2-b] pyridazin-8-amine (301 mg, 70 %) as a yellow solid. LC-MS : [M+H]+, 329.1 , tR = 1.949min.

The chemical industry reduces the impact on the environment during synthesis 933190-51-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
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1996-30-1, Name is 3-Bromo-4-fluorochlorobenzene, 1996-30-1, 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.

To a solution of 2-bromo-4-chloro-1 -fluorobenzene (1 .03 g, 4.94 mmol) in tetrahydrofuran (20 ml_) at -78 C was added n-butyllithium (4.0 ml_, 9.88 mmol) under nitrogen. The reaction mixture was stirred at -78 C for 2 h before a solution of 6-(4-methoxybenzylamino)pyridazine-3-carbaldehyde (0.800 g, 3.29 mmol) in tetrahydrofuran (3 ml_) was added dropwise. The reaction mixture was stirred for another 2 h and was warmed to 20 C. Aqueous ammonium chloride was added to quench the reaction and the volatiles were removed under reduced pressure. The aqueous layer was extracted with dichloromethane (50 ml_ x 2). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude sample was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4/1 to 1 /1 ) to give (5-chloro-2-fluorophenyl)(6-(4-methoxybenzylamino)pyridazin-3-yl)methanol (0.330 g, 0.888 mmol, 27%) as a yellow solid. LCMS (ESI) m/z: 374.0 [M+H]+.

Statistics shows that 3-Bromo-4-fluorochlorobenzene is playing an increasingly important role. we look forward to future research findings about 1996-30-1.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, A new synthetic method of this compound is introduced below., 27139-97-5

To a suspension of magniesium (0.12 g) in THF (15 ml_) 2-bromo-4-chlorotoluene (0.125 g, commercially available) was added and the mixture stirred for a few minutes. Then a solution of 2-bromo-4-chlorotoluene (0.9 g) in THF (85 ml_) was added dropwise and the mixture stirred for 3h. The mixture was added dropwise to a solution of acetyl chloride(0.353 g) in THF (10 ml_) at 0 0C. The mixture was stirred at RT for 5h. Chilly water was added to the reaction mixture and the pH adjusted at pH 6 with HCI 10percent and the product extracted with EA. The organic phase was dried and the solvent evaporated under vacuum to give the title compound (0.676 g) that was used in next step without further purification.MS (m/z): 169 [MH]+

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; GLAXO GROUP LIMITED; WO2009/130231; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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.

Reference Example-10 A solution of 1-bromo-4-chloro-2-fluoro benzene (10.0 g, 47.8 mmol) in THF was added dropwise to a suspension of magnesium (1.28 g, 52.5 mmol) in THF (50 mL) at 40 C. (oil bath temperature) in the presence of a catalytic amount of iodine in an argon gas atmosphere, whereby a Grignard reagent was prepared. The Grignard reagent was added dropwise to a solution of diethyl oxalate (8.37 g, 57.3 mmol) in THF at -50 C., and the temperature was slowly raised to room temperature, followed by stirring for 18 hours. After the reaction was completed, the reaction solution was poured into ice, then, acidified with concentrated hydrochloric acid, and the resultant product was extracted with ether (100 mL*2, 50 mL*1). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, whereby an orange oily crude product (12.9 g) was obtained. This was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), whereby ethyl 2-(4-chloro-2-fluorophenyl)-2-oxoacetate (4.17 g, yield: 41%) was obtained as a yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.40 (t, J=7.1 Hz, 3H), 4.43 (q, J=7.1 Hz, 2H), 7.22 (dd, J=1.8 and 10.2 Hz, 1H), 7.31 (dd, J=1.8 and 8.4 Hz, 1H), 7.89 (dd, J=7.6 and 8.4 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-109 (s, 1F).

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 1996-29-8.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, I believe this compound will play a more active role in future production and life. 56961-77-4

Example 1 1- (2, 3-DICHLOROPHENYL)- [1, 4] diazepine (starting material) 2.25 g (10 MMOL) 1-bromo-2, 3-dichloro-benzene was dissolved in dry toluene (50 ml), 2.3 (11 MMOL) of [1, 4] diazepine-1-carboxylic acid tert-butylester was added followed by 0.2 g BINAP (2,2-bis (diphenylphosphino)-1, 1′-binaphtyl), 85 mg tris (DIBENZYLIDENEACETONE) dipalladium (0) and 1.2 g (12MMOL) SODIUM-TERT-BUTOXYDE. The reaction mixture was refluxed for eight hours and filtered. The organic layer was washed with water, dried and evaporated in vacuo. The residue was purified by chromatography and deprotected at 10 C using 20 ML ETHYLACETATE saturated with gaseous hydrochloric acid, the precipitate was filtered giving 2.1 g (yield : 75 %) hydrochloride salt of the title compound, melting at 182-3 C.

The chemical industry reduces the impact on the environment during synthesis 56961-77-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2005/12266; (2005); 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1996-30-1

Step 1. l-(2-Bromo-4-chlorophenyl)-lH-l,2,3-triazole. To a solution of 2-bromo-4-chloro-l- fluorobenzene (5 g, 24 mmol) and 2H-l,2,3-triazole (6.60 g, 95 mmol) in DMF (2 mL) was added K2CO3 (16.50 g, 119 mmol). The mixture was stirred at 100C for 13 h under N2 atmosphere. The mixture was diluted with water (10 mL) and extracted with EtOAc (10 mL x 2). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (Si02, PE: EtOAc = 100: 1 to 3: 1) to give the title compound. MS (ESI) m/z 260.0 (M+H).

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Weiguo; EDMONDSON, Scott, D.; GUO, Zhuyan; MERTZ, Eric; OGAWA, Anthony, K.; SO, Sung-Sau; SUN, Wanying; BROCKUNIER, Linda, L.; ALI, Amjad; KUANG, Rongze; WU, Heping; WO2015/183709; (2015); A1;,
Chloride – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 823-57-4, name is 2-Bromo-5-chloroaniline, I believe this compound will play a more active role in future production and life. 823-57-4

Step B: Preparation of l-Bromo-4-chloro-2-iodobenzene; [0828] A suspension of 2-bromo-5-chlorobenzenamine (1 1.348 g, 54.963 mmol) in concentrated HCl (100 mL) was cooled to 0C and treated dropwise over 20 minutes (using an addition funnel) with a solution of sodium nitrite (4.5506 g, 65.955 mmol) in water (20 mL). The reaction was stirred at 00C for 75 minutes. A solution of potassium iodide (27.372 g, 164.89 mmol) in water (50 mL) was added, and the reaction was stirred at 23C. After 1 hour, the reaction was heated to 700C. After 18 hours, the reaction was diluted with EtOAc (500 mL) and washed with water (300 mL), 2N NaOH solution (300 mL), saturated sodium thiosulfate solution (300 mL) and brine (250 mL), dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (eluant: hexane) affording 1 1.1 1 g of 1 -bromo^-chloro^-iodobenzene.

The chemical industry reduces the impact on the environment during synthesis 823-57-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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. 2770-11-8.

2-(4-Chlorophenoxy)aniline (200 mg, 0.9107 mmol, 1.1 eq) and JV-(3-acetylphenyl)-iV- ethylacetamide (169 mg, 0.827 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (395 muL, 1.654 mmol, 2 eq) was added to the reaction mixture which was stirred at room temperature for 16 hours. Sodium triacetoxyborohydride (700 mg, 3.308 mmol, 4 eq) was then added to the reaction mixture and was stirred at room temperature for a further 24 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (120 mL). The organic layer was washed with brine (120 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 25% ethyl acetate in petrol ether to 50% ethyl acetate in petrol ether] gave (87 mg, 26 %) as a white solid. 1H NMR (270 MHz, CDCl3) delta 1.05 (3H, t, J = 8.1 Hz, CH3), 1.49 (3eta, d, J = 6.4 Hz CH3), 1.67 (3H, s, CH3), 3.68 (2H, q, J= 8.1 Hz, CH2), 4.45-4.60 (2H, m, NH and CH) 6.37 (1eta, d, J = 8.2 Hz, ArH), 6.57 (IH, dt, J = 1.4, 8.2 Hz ArH), 6.75-7.06 (6H, m, ArH), 7.23-7.39 (4H, m, ArH); 13C NMR (67.5 MHz, CDCl3) delta 13.1, 22.8, 25.0, 43.8, 52.8, 112.0, 112.9, 117.2, 118.7, 119.3, 125.0, 126.1, 126.5, 128. 0, 129.8, 130.0, 138.0, 139.1, 142.8, 147.1, 156.5, 169.9 LCMS (90% MeOH and 10% H2O; Symmetry C18 reverse phase column) tr = 2.88 min; (ES+), m/z 409.2 (35ClM’, 75%), 383 (37ClM’, 25%); HRMS (ESI) calcd. for C24H25ClN2O2 (M+H)+ 409.1605, found 409.1689. 99.48% purity.

The synthetic route of 2-(4-Chlorophenoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics