Month: December 2020

Related Products of 2905-54-6,Some common heterocyclic compound, 2905-54-6, name is Methyl 2,3-dichlorobenzoate, molecular formula is C8H6Cl2O2, 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.

b) (2,3-dichlorophenyl)methanol A suspension of LiAlH4 (7.4 g, 0.195 mol) in THF (500 mL) was stirred at 0 C. A solution of methyl 2,3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 mL) was added dropwise into the above mixture at 0-5 C. Then the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15% NaOH (7.5 mL) and water (22.5 mL), filtered and the filtrate was concentrated. The resulting residue was dissolved with DCM (500 mL) and washed with brine. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (37 g, 88%), as a white solid; 1H NMR (300 MHz, CDCl3) delta ppm 4.81 (d, J=6.3 Hz, 2H), 7.24 (t, J=7.8 Hz, 1H), 7.42-7.45 (m, 2H).

The synthetic route of 2905-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline LLC; Lin, Hong; Luengo, Juan Ignacio; Moore, Michael Lee; Qu, Junya; Rivero, Ralph A.; Tedesco, Rosanna; Yu, Hongyi; US9096605; (2015); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 541-16-2, The chemical industry reduces the impact on the environment during synthesis 541-16-2, name is Di-tert-Butyl malonate, I believe this compound will play a more active role in future production and life.

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

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, Di-tert-Butyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, belongs to esters-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 13831-03-3, COA of Formula: C7H10O2

The methyl 5-chloro-2-(3-fluorophenyl)nicotinate (1.00 g, 3.76 mmol) was combined with freshly prepared 2-[(aminooxy)sulfonyl]-l,3,5-trimethylbenzene (0.972 g, 4.52 mmol) ether solution in acetonitrile (20.0 rnL) at room temperature. The reaction was stirred for 24 hours and became a tan colored slurry. The slurry was added portion wise to a vigorously stirring suspension of tert-butyl propiolate (1.55 mL, 1 1.3 mmol), N,N-dimethylformamide (20.0 mL, 258 mmol) and potassium carbonate (2.60 g, 18.8 mmol) open to the air. After stirring for 15 minutes, the reaction was a dark red brown suspension. This was allowed to stir for 5 hours at room temperature. The reaction was taken up in ethyl acetate and decanted from the solids. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a reddish brown oil. The product was purified on silica gel eluting hexane: ethyl acetate gradient to give 3-tert-butyl 6-methyl 4- chloro-7-(3-fluorophenyl)pyrazolo[l,5-a]pyridine-3,6-dicarboxylate (0.46 g, 30%) as a semisolid residue. LCMS calculated for C2oH19ClF 204 (M+H)+: m/z = 405.1 ; found: 404.9.

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

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; SPARKS, Richard B.; YUE, Eddy W.; WO2011/130342; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 40872-87-5,Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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.

To a mixture of methyl 3-amino-4-chlorobenzoate (10 g, 54 mmol) and aqueous HC1 solution (12 M, 15 mL) in water (80 mL) at 0 C was added dropwise a solution of NaNO2 (4.5 g, 60 mmol) in water (18 mL) at 0 C. The reaction was stirred for 30 mm at 0 C and then added dropwise to a sluny of CuCN (4.9 g, 54 mmol) and KCN (6.0 g, 92 mmol) in water (40 mL), while maintaining the temperature between 5-10 C. The reaction mixture was stined at 10 C for 30 mm and then heated at 80 C for 1 h. After cooling, the mixture was extracted with DCM. The organic layer was washed with brine, dried over Na2504 and then concentrated to afford the title compound. MS: m/z = 196.0 (M + 1). ?H NMR (400 MHz, CDC13) oe 8.34 (d, J 2.0 Hz, 1H), 8.17-8.20 (m, 1H), 7.61 (d,J= 8.4 Hz, 1H), 3.96 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-4-chlorobenzoate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2967-66-0,Some common heterocyclic compound, 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, molecular formula is C9H7F3O2, 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.

Several others esters (see Table 3) were hydrogenated under identical conditions as reported in Table 4 with RuCl2(L-I)2. The reaction conditions were identical to those reported above for methyl benzoate.Table 3: Structure and name of substrates used EPO Table 4: Results obtained using the general conditions described above EPO Conversion: (in %, analysed by GC after silylation) of ester to alcohol after 2h 30min. Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I)2 0.05 mol%, NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; FIRMENICH SA; WO2006/106483; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 69812-51-7, 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. 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of cytisine (2 mmol) in dichloromethane (30 mL), triethylamine (2.4 mmol), and 4-methoxycarbonyl benzenesulfonyl chloride (2.2 mmol) were added and stirred at room temperature until the TLC analysis showed completion of the reaction. Then the reaction solution was washed with water and brine. The organic phase was dried with anhydrous sodium sulfate and concentrated to give a residue, which was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent and then acidified with 2 N HCl/Et2O to give the title compounds. Yield: 85%; white solid; mp: 112-114 C. 1H NMR (600 MHz) delta 7.73 (t, J=6.0 Hz, 1H), 7.68-7.62 (m, 2H), 7.59 (d, J=7.2 Hz, 1H), 7.36 (dd, J=8.4, 7.2 Hz, 1H), 6.24 (d, J=8.4 Hz, 1H), 6.18 (d, J=6.0 Hz, 1H), 3.84 (s, 1H), 3.81 (s, 3H), 3.78-3.70 (m, 2H), 3.65-3.64 (m, 1H), 3.19 (s, 1H), 2.92-2.81 (m, 2H), 2.52 (s, 1H), 1.85-1.78 (m, 2H); 13C NMR (151 MHz) delta 168.2, 162.5, 150.1, 139.5, 134.4, 133.5, 133.4, 131.2, 128.9, 128.6, 116.6, 105.2, 53.3, 53.1, 52.1, 49.0, 33.8, 26.8, 24.3. HRMS: calcd for C19H21N2O5S [M+H]+ 389.1166, found: 389.1155.

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 4-chlorosulfonylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tang, Sheng; Li, Yinghong; Bao, Yunyang; Dai, Zhiting; Niu, Tianyu; Wang, Kun; He, Hongwei; Song, Danqing; Bioorganic Chemistry; vol. 90; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1150566-27-0,Some common heterocyclic compound, 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, molecular formula is C9H8ClN3O2, 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.

[0418] Step 1. 6- [(5-Fluoro-2-hydroxy-benzyl)-methyl-amino] -imidazo [1 ,2-b]pyridazine-3- carboxylic acid ethyl ester (42B). To a mixture of 4-fluoro-2-methylaminomethyl-phenol (20L, 305.2 mg, 1.97 mmol) and 6-chloro-imidazo [1 ,2-b]pyridazine-3-carboxylic acid ethyl ester (42A, 230 mg, 1.02 mmol) in DMSO (5 mL) was added KF (180 mg, 3.01 mmol). The reaction mixture was stirred at 120 C for 18 hours under nitrogen. The solution was then cooled to ambient temperature, diluted with water (20 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were further washed with water (3 x 50 mL) and brine (50 mL), dried over Na2504 and concentrated. The residue was then purified by a silica gel column eluting with EtOAc/hexane (0-50%, 10 CV) to afford the desired product as a white solid (240 mg, 69%). LC-MS (ESI) m/z 345.2 (M+H) ?H NMR (500 MHz, chloroform-d) oe 8.61 (s, 1H),8.17 (s, 1H), 7.91 (d, J= 10.0 Hz, 1H), 7.00-6.86 (m, 4H), 4.78 (s, 2H), 4.47 (qd, J= 7.2, 0.5 Hz, 2H), 3.17 (s, 3H), 1.41 (td, J= 7.1, 0.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, its application will become more common.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 66315-16-0, The chemical industry reduces the impact on the environment during synthesis 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, I believe this compound will play a more active role in future production and life.

1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester may be prepared from 3-amino-4-methylamino-benzoic acid methyl ester, 2-amino-6-(trifluoromethoxy)benzothiazole, 1,1?-thiocarbonyl-diimidazole, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). 1,1?-Thiocarbonylimidazole may be added to a solution of 2-amino-6-(trifluoromethoxy)benzothiazole in DMF, and the reaction mixture stirred at 90-100 C. for a day. To this reaction mixture at room temperature is added EDC and stirred at 60 C. for 5 min. To this reaction mixture at room temperature is added 3-amino-4-methylamino-benzoic acid methyl ester and stirred at 90 C. The reaction mixture may then be cooled to room temperature, poured into ice-cold water and the solid collected by filtration. The crude product thus obtained may be purified by trituration with dichloromethan-methanol (9:1). LC/MS: m/z 423.8 (M+1)+.

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 3-amino-4-(methylamino)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; vTv Therapeutics LLC; Kassis, Jareer Nabeel; Attucks, Otis Clinton; Kostura, Matthew J.; (41 pag.)US2017/56413; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 541-16-2, 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 541-16-2 as follows.

To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NAOH solution (92.4 g in 185 mL H20) was added 1,2- dibromobutane (30.0 g, 138.9 mmol) and DI-TERT-BUTYLMALONATE (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred 18 h at rt, a mixture of ice and water was then added. The crude product was extracted with CH2CI2 (3x) and sequentially washed with water (3x), brine and the organic extracts combined. The organic layer was dried (MgS04), filtered and concentrated in vacuo. The resulting residue was flash chromatographed (100 G SI02, 3% ET20 in hexane) to afford the titled product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99316; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 17435-72-2, 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. 17435-72-2, name is Ethyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 6 Synthesis of ethyl 2-Phenoxymethylacrylate A solution of ethyl 2-bromomethylacrylate (2.00 g, 10.4 mmol, ref: Villieras, J. and Rambaud, M. Synthesis, 1982, 914) and phenol(975 mg, 1.0 eq) in dry THF (20 ML) under N2 at 0 C. was treated with anhydrous K2CO3 (1.43 g, 1.0 mol eq).. No reaction was observed for 1 h.. anhydrous DMF (20 ML) was added and stirred for 2 h at 0 C. and for 1 h at room temperature.. After evaporation of DMF, water(100 ML) was added, and the reaction was extracted with ethyl acetate (100 ML*2).. The organic extract was washed with brine (100 ML), dried (anh. Na2SO4), filtered and concentrated.. Flash chromatography (40% CH2Cl2/hexanes) gave 1.712 g (80%) of the title compound. 1H-NMR (500 MHz, CDCl3) delta 7.30 (2H, yt, J=7.3 Hz), 6.99-6.96 (3H, m), 6.41 (1H, s), 6.01 (1H, s), 4.78 (2H, s), 4.27 (2H, q, J=7.33 Hz).

The synthetic route of Ethyl 2-(bromomethyl)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem Investment Ltd.; US6747050; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics