Tag: M.W=200-300

Application of 39226-96-5,Some common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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: Compound 2a (438mg, 2.5mmol) and 2-chloro-3-(trifluoromethyl)benzylamine (419mg, 2.0mmol) were mixed with EDAC (480mg, 2.5mmol) and 1-hydrobenzotrizole (HOBt, 338mg, 2.5mmol) in dry dichloromethane (60mL). The reaction mixture was stirred for overnight at RT. Then the resultant mixture was washed with 2N HCl (50mL) and saturated aqueous NaHCO3 (40mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel with eluent (2:98 MeOH/CH2Cl2) to afford a white solid product 3a (210mg, 28%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, its application will become more common.

Reference:
Article; Gao, Mingzhang; Wang, Min; Glick-Wilson, Barbara E.; Meyer, Jill A.; Peters, Jonathan S.; Territo, Paul R.; Green, Mark A.; Hutchins, Gary D.; Zarrinmayeh, Hamideh; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1603 – 1609;,
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Adding a certain compound to certain chemical reactions, such as: 873-38-1, name is 2-Bromo-4-chloroaniline, 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 873-38-1, Computed Properties of C6H5BrClN

General procedure: Compound 15 (67.5 g, 0.355 mol) was added to the 300 mL 15 % aq. HCl. A resulting suspension was stirred for 1 h at 80 oC, then cooled to -5 C and NaNO2 (26.0 g, 0.365 mol) in H2O (50 mL) was slowly added. The mixture was stirred for 1.5 h at -5 C and then the excess of HNO2 was neutralized with urea. The solution of KI (57.2 g, 0.0355 mol) in 50 mL H2O was added dropwise at 0 oC (caution, the fast evolution of N2 was observed). The mixture was warmed to room temperature and stirred for 40 h. After this time CHCl3 was added, water phase was extracted with CHCl3 (3 × 100 mL), joined organic phases were washed with saturated solution of NaHCO3 (200 mL), 5% solution of Na2S2O3 (200mL) and5% solution of Na2S2O5 (200mL). Organic phase was dried over MgSO4 and concentrated under reduced pressure. The obtained crude product was distilled under reduced pressure (b.p. 90-91 oC, 2 Tr) affording 17 as viscous oil (69.1 g, 64%).

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

Reference:
Article; Durka, Krzysztof; Laudy, Agnieszka E.; Charzewski, ?ukasz; Urban, Mateusz; St?pie?, Karolina; Tyski, Stefan; Krzy?ko, Krystiana A.; Luli?ski, Sergiusz; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 11 – 24;,
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Electric Literature of 62356-27-8, The chemical industry reduces the impact on the environment during synthesis 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

Take a 500 ml double-necked round bottom bottle and place it in a stirrer with a reflux tube. After drying, it is filled with nitrogen. First, add compound A-1 (20.548 g, 1.0 equivalent) and NBS (N-bromosuccinimide). , 19.5778 grams, 1.1 equivalents),And AIBN (azobisisobutyronitrile, 0.821 g, 0.5 mol%), followed by the addition of carbon tetrachloride (250 ml) and stirred for 10 minutes.Finally heated to reflux and reacted for 24 hours;After warming-up, water (200 ml) was added, followed by extraction with ethyl acetate (3×200 ml), and the obtained extract was sequentially dried over magnesium sulfate, filtered and evaporated to dryness. Ethyl acetate/hexane, 1/10) gave Intermediate 1-1 (21.044 g, yield 74%).

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, 1-Bromo-3-chloro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ningbo Lumilan New Materials Co., Ltd.; Ningbo Jizhichuang New Materials Institute Co., Ltd.; Wei Dingwei; Xie Kunshan; Chen Zhikuan; (50 pag.)CN109651423; (2019); A;,
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Related Products of 766545-20-4, 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. 766545-20-4 name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, 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.

2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (2.00 g, 9.75 mmol, 1.00 eq) was dissolved in DCM (20.00 mL) and triethylamine (2.47 g, 24.38 mmol, 2.50 eq) and di-tert-butyl dicarbonate (3.19 g, 14.63 mmol, 1.50 eq) were added at 15 C under the nitrogen gas atmosphere. The mixture was stirred at 15 C for 12 hours. The mixture was poured into water (30 mL) and the aqueous phase was extracted with dichloromethane (100 mL * 4). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to deliver tert-butyl 2-chloro-7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate (2.50 g, 9.30 mmol, 95.41% yield) as a white solid. LCMS (ESI) m / z: 269 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Medshine Discovery Inc.; LUO, Wei; DING, Charles Z.; HUANG, Zhigang; CHEN, Shuhui; (162 pag.)EP3252059; (2017); A1;,
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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. 16799-05-6, name is 3-Chlorophenethyl Bromide, A new synthetic method of this compound is introduced below., Formula: C8H8BrCl

Example 15: Preparation of 8-r2-(3-chlorophenyl)ethvn-3-methyl-4-((4-r3- (trifluoromethyl)phenvnpiperazin-1-yl}carbonyl)-1-oxa-8-azaspiror4.5ldec-3-en-2-oneA mixture of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1 -oxa-8- azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 200 mg, 0.40 mmol), anhydrous potassium carbonate (180 mg, 1.30 mmol) and 1-(2-bromo-ethyl)-3-chloro-benzene (0.07 mL, 0.22 mmol) in anhydrous Nu,Nu-dimethylformamide (3 mL) was heated at 90C for 1.5 hours under microwave irradiation. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane (20 mL), washed with water (20 mL) and brine (20 mL), dried (MgS04) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid. 1H NMR (DMSO-d6, 400 MHz): delta 7.46-7.42 (m, 1 H), 7.30-7.17 (m, 6H), 7.11 (d, J = 7.5 Hz, 1H), 3.79-3.78 (m, 1H), 3.68-3.67 (m, 1H), 3.55 (s, 3H), 3.55 (d, J = 4.9 Hz, 2H), 2.89-2.88 (m, 3H), 2.73-2.71 (m, 2H), 2.49-2.48 (m, 2H), 2.23-2.21 (m, 3H), 1.82-1.81 (m, 1 H), 1.75 (s, 3H), 1.67-1.66 (m, 1 H), 1.51-1.49 (d, J = 7.3 Hz, 1H). LCMS (Method D): Mass found (M+ 562), Rt (min): 4.75, Area (%): 99.6 (Max), 99.5 (254 nm). HPLC (Method A): Rt (min): 4.72, Area (%): 99.3 (Max), 99.2 (254 nm).

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; ARES TRADING S.A.; JORAND-LEBRUN, Catherine; SWINNEN, Dominique; GERBER, Patrick; KULKARNI, Santosh; WO2012/130915; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 110407-59-5, These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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.

General procedure: NiCl2(PCy3)2 (17 mg, 0.025 mmol) was added to a substrate (0.5 mmol) in dry THF (4 mL – 10 mL) and then LiAl(O-t-Bu)3H (2 mmol – 8 mmol, ) was added to this solution slowly under argon atmosphere. The mixture was then heated to reflux and left to stir while being periodically monitored by GC and GC/MS. All products were identified by GC/MS and GC.

Statistics shows that 2-Chloro-4-fluorobromobenzene is playing an increasingly important role. we look forward to future research findings about 110407-59-5.

Reference:
Article; Xiao, Juan; Wu, Jingjing; Zhao, Wenwen; Cao, Song; Journal of Fluorine Chemistry; vol. 146; (2013); p. 76 – 79;,
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Related Products of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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.

Reference 7; Synthesis of 2-(3-bromo-5-chlorophenyl)propanoic acid Step 1A heavy- wall flask was charged with sodium hydride (9.5 g, 239 mmol) (60% oil dispersion) in NMP (75 ml) under a positive nitrogen flow. Ethyl 2-cyanoacetate (27 g, 239 mmol) was added in a dropwise manner. The reaction mixture was stirred until no more bubbling was observed. l-Bromo-3-chloro-5-fluorobenzene (10.00 g, 48 mmol) was added to the reaction mixture. The flask was capped and the reaction mixture was heated to 115 0C. After 15 hours, the reaction mixture was cooled down and diluted with water. The pH of the reaction mixture was adjusted to 3 with 2N HCl and extracted with ether. The organics were combined and washed with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 5 to 40 % EtOAc in hexanes to give ethyl 2-(3-bromo-5-chlorophenyl)-2-cyanoacetate (10.00 g, 69% yield) as a white semi solid.

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-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/75874; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 468075-00-5, 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. 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of ethyl 2-(3-(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate (140 mg, 0.553 mmol), cesium carbonate (540 mg, 1.66 mmol), 2-bromo-1-chloro-4-(trifluoromethoxy)benzene (0.175 ml, 1.105 mmol) and (RuPhos)palladium(II) phenethylamine chloride (40.3 mg, 0.055 mmol) in 1,4-dioxane (3 ml) in amicrowave reaction vial was bubbled with nitrogen. The vial was sealed and the mixture was stirred overnight in an oil bath kept at 100C. The mixture was diluted with aq. NH4Cl solution and extracted 3 times with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by chromatography eluting with 0-10%-20% ethyl acetate-hex to give ethyl 2-(3 -(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate. LCMS m/z 448.13 [M+H]+.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHELLIAH, Mariappan; CHU, Hong Dong; COX, Jason, M.; DEBENHAM, John, S; EAGEN, Keith; LAN, Ping; LONDON, Clare; PLOTKIN, Michael, A.; SHAH, Unmesh; SINZ, Christopher Joseph; SUN, Zhongxiang; VACCARO, Henry, M.; VENKATRAMAN, Skikanth; WO2014/59232; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 56961-77-4, 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. 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[Intermediate 5-1] 10 g of 30.2 mmol was dissolved in 100 mL of xylene, followed by the addition of 8.7 g of NatBuO, stirring at 180 C., and then 3.41 g of 1-bromo-2,3-dichlorobenzene and 0.37 g Give it in sequential order. After 12 h, the reaction was quenched with NH4Cl, extracted with EA, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.This was columned with EA: Hx to obtain 7.2 g (Yield 62%) of [Intermediate 17-1].

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

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Yoon Jeong-min; Kim Gong-gyeom; Huh Nan-seul-a; Lee Gi-gon; Keum Su-jeong; (52 pag.)KR2018/112721; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 7464-11-1,Some common heterocyclic compound, 7464-11-1, name is 5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine, molecular formula is C6H3Cl2N3S, 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 50-mL round-bottom flask, was charged with a solution of intermediate 41.2 (111 mg, 0.49 mmol, 1.00 equiv) in CH3CN(10 mL), K3P04 (322 mg, 1.52 mmol, 3.07 equiv), and compound 23.1 (125 mg, 0.57 mmol, 1.15 equiv). The reaction was stirred overnight at 85 C in an oil bath. Solids were filtered out and solution was concentrated under vacuum. The crude product obtained was purified using flash column chromatography to yield 180 mg (89%) of intermediate 41.3 as a yellow solid.

The synthetic route of 7464-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics