Tag: M.W:200-300

Reference of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, The 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.

To a solution of 5-bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 0C, was added oxalyl dichloride (16.98 mL, 194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reactionmixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm)Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 78607-36-0 ,Some common heterocyclic compound, 78607-36-0, molecular formula is C5H3ClIN, 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.

Dissolve 2-chloro-3-iodopyridine (2.0 g, 8.37 mmol) in toluene (7 mL). Add piperazine-1-carboxylic acid t-butyl ester (1.2 g, 6.4 mmol), followed by the addition of tris(dibenzylideneacetone)dipalladium(0) (0.12 g, 0.13 mmol), 4,5-bis(diphenyl- phosphino)-9,9-dimethylxanthene (0.23 g, 0.39 mmol), and sodium t-butoxide (0.93 g, 9.7 mmol). Heat at 100 0C for 3.5 hr. Concentrate and partition the residue between EtOAc and water. Extract the aqueous phase twice with ethyl acetate. Wash combined organic layers with brine. Dry the organic extracts (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0: 100 to 20:80 ethyl acetate:hexanes), to give the title preparation (95%). MS (ES): m/z = 298 [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,78607-36-0, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/29439; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1970-81-6, name is [3,3′-Bipyridine]-5-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.Recommanded Product: 1970-81-6

Referring to Scheme 1, synthesis of compound 13, to a cooled (0C) suspension of compound 2 (0.6 g, 3.0 mmol) in dichloromethane (100 mL), was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.69 g, 3.6 mmol), 1-hydroxy-benzotriazole hydrate (0.49 g, 3.6 mmol), and triethylamine (0.5 mL, 3.6 mmol). After stirring for 30 min. at 0C (the reaction became almost clear), compound 9 (0.4 g, 1.2 mmol) and triethylamine (1.0 mL, 7.2 mmol) were added. The reaction was stirred for 16 h., then washed with saturated NaHCO3 (3 x 50 mL). The DCM layer was dried with MgSO4, reduced in volume in vacuo, and purified by flash column chromatography (2% – 25% methanol in DCM) to give compound 13 (90 mg, 12%). 1H NMR (CDCl3, 500 MHz) delta 1.70 (m, 2H), 1.75 (m, 2H), 1.87 (m, 2H), 1.89 (s, 3H), 1.98 (m, 1H), 2.14 (m, 1H), 3.28 (m, 1H), 3.35 (m, 1H), 3.40 (m, 2H), 3.64 (m, 1H), 3.70 (m, 1H), 4.85 (q, J = 4.9 Hz, 1H), 5.30 (s, 1H), 5.67 (s, 1H), 6.40 (t, J = 5.0 Hz, 1H), 7.36 (t, J = 5.0 Hz, 1H), 7.42 (dd, J = 3.9, 2.2 Hz, 1H), 7.43 (dd, J = 3.9, 2.2 Hz, 1H), 7.65 (t, J = 4.45 Hz, 1H), 7.72 (d, J = 6.1 Hz, 1H), 7.93 (d, J = 1.5 Hz, 1H), 7.95 (d, J = 1.5 Hz, 1H), 8.42 (m, 2H), 8.67 (dd, J = 4.1, 1.0 Hz, 1H), 8.68 (dd, J = 4.0, 1.2 Hz, 1H), 8.889 (s, 1H), 8.891 (s, 1H), 8.93 (d, J = 1.7 Hz, 1H), 8.96 (d, J = 1.8 Hz, 1H), 9.10 (d, J = 1.6 Hz, 1H), 9.13 (d, J = 1.7 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1970-81-6, [3,3′-Bipyridine]-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MEDTRONIC MINIMED, INC.; GAMSEY, Soya; WESSLING, Ritchie, A.; EP2222686; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 171178-46-4 , The common heterocyclic compound, 171178-46-4, name is 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid, molecular formula is C11H13ClN2O4, 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.

5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinic acid (Intermediate B) (4.27 g, 15 mmol, 1 equiv.) was added to a 500 mL two necked oven-dried round bottom flask equipped with a stirring bar and suspended in dichloromethane (187 mL, 0.08M) was added. 4-Dimethylamino pyridine (7.40 g, 60 mmol, 4 equiv.) was added at 22C resulting in an homogeneous solution. /V-(3-dimethylaminopropyl)-/V-ethylcarbodiimide (4.65 g, 30 mmol, 2 equiv.) was added at that temperature and the crude mixture was stirred for 3 h. Anhydrous MeOH (HPLC quality), (5.5 mL, 135 mmol, 9 equiv.) was added to the solution and the mixture was stirred for 1 h at 22C. The resulting mixture was heated to reflux using an aluminium heating block for 72 h. TLC (EtOAc:MeOH 90:10 %v/v) showed complete conversion of Intermediate B into Intermediate C. The reaction was permitted to reach to 22C and volatiles were removed under reduced pressure. Dichloromethane (150 mL) was added to the residue until complete solution was achieved and the mixture was transferred to a separating funnel, washed with H2O (1 x 70 mL), HCI 1 M (2 x 50 mL) and saturated NaCI solution (1 x 50 mL). The organic phase was dried with Na2S04 and filtered through a pad of Na2S04 on a filter plate. The solvent was removed under reduced pressure giving a brown solid, which was purified by automated flash chromatography (Heptane:EtOAc, product elution with EtOAc 100%v/v) giving methyl 5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinate as a pale yellow solid (4.04 g, 79% yield). Purity: 99.4% (UPLC-A); mp: 90.0-95.8 C; 1H- NMR (CDCI3), 5(ppm): 9.68 (bs, NH), 9.49 (s, 1 H), 7.73(s, 1 H), 7.20 (s, 1 H), 3.91 (s, 3H), 1.47 (s, 9H); LR-MS (ESI+): m/z= 287.1 Da [M+H]+, calcd. for CI2HI5CIN204: 286.2

The synthetic route of 171178-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAES FARMA, S.A.; HERNANDEZ HERRERO, Gonzalo; GARCIA DOMINGUEZ, Neftali; ZAZPE ARCE, Arturo; OLIVERA TIZNE, Roberto; NOVERGES PEDRO, Barbara; CORCOSTEGUI VIVAR, Reyes; TATO CERDEIRAS, Paloma; (124 pag.)WO2020/20939; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929000-66-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.929000-66-8, name is 3-Bromo-6-chloropyridine-2-carboxylic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.4505, as common compound, the synthetic route is as follows.

A mixture of 3-bromo-6-chloropyridine-2-carboxylic acid (10.0 g, 42.2 mmol, CAS 929000-66-8) in MeOH (100.0 mL)/SOCl2 (10.0 mL) was stirred at 80 C for 3 hours. The reaction mixture was concentrated in vacuo to give methyl 3-bromo-6-chloropyridine-2- carboxylate (10.4 g, 99% yield) as a yellow solid.

Statistics shows that 929000-66-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-chloropyridine-2-carboxylic acid.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 624-28-2, 2,5-Dibromopyridine, 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, Product Details of 624-28-2, blongs to pyridine-derivatives compound. Product Details of 624-28-2

3.1. 1,1-dimethylethyl 4-(5-bromo-2-pyridyl)-1-piperazinecarboxylate 29.2 g (157 mmol) of 1,1-dimethylethyl 1-piperazine-carboxylate, 37 g (157 mmol) of 2,5-dibromopyridine and 21.7 g (157 mmol) of potassium carbonate suspended in 27 ml of dimethyl sulfoxide (DMSO) are introduced into an autoclave. The mixture is then heated at 150 C. for 21 hours. The reaction mixture is allowed to cool to room temperature, it is taken up in ethyl acetate and water and the insoluble material is then separated out by filtration. The aqueous phase is separated out and extracted twice with ethyl acetate, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel, eluding with a 99/1 mixture of dichloromethane and methanol. 44 g of product are thus obtained in the form of a white solid. m.p. ( C.): 83-85 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,624-28-2, 2,5-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2006/293310; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 851386-34-0, 2,3-Difluoro-4-iodopyridine, 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, Formula: C5H2F2IN, blongs to pyridine-derivatives compound. Formula: C5H2F2IN

Tetrakis(triphenylphosphine)palladium(0) (1.91 mg, 1.66 mmol) was added to a solution of methyl 3-amino-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-nitrobenzoate (6.1 g, 19.9 mmol), 2,3-difluoro-4-iodopyridine (4.0 g, 16.6 mmol), and potassium phosphate tribasic (10.6 g, 49.8 mmol) in dioxane (80 mL) and water (20 mL). Nitrogen was bubbled for 10 minutes and the reaction mixture was stirred at 80° C. for 10 hours. Upon cooling, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 5 to 70percent of (5percent methanol in ethyl acetate) in hexane to afford methyl 3-amino-5-(2,3-difluoropyridin-4-yl)-2-nitrobenzoate. ES/MS m/z=310.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851386-34-0, 2,3-Difluoro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Gilead Sciences, Inc.; Chandrasekhar, Jayaraman; Patel, Leena; Perreault, Stephane; Phillips, Gary; Till, Nicholas Alexander; Treiberg, Jennifer Anne; (118 pag.)US2018/86768; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 38940-62-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.38940-62-4, name is 3-Acetyl-5-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.

Commercially available 3-acetyl-5- bromopyridine (6.53 g, 32.8 mmol), solid NaOH (13.1 g, 326 mmol), and hydrazine hydrate (13 mL) was heated in di ethylene glycol (25 mL) at 140 0C for 4 hours. The reaction mixture was partitioned between ether and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give an oil. This was dissolved in tetrahydrofuran (40 mL) and cooled to 0 0C. Isopropylmagnesiumchloride (20 mL, 2.0 M in THF) was syringed in and the reaction mixture was stirred for 2 hours at room temperature. N,N-dimethylformamide (7 mL) in tetrahydrofuran (15 mL) was added and stirring was continued for. an additional hour. The solution was quenched with 2 N HCl to pH of 3 then partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give 3- ethyl-5-formylpyridine (0.78 g, 18%) as a solid. 1H NMR (DMSO-^6): delta 10.1 (s, IH), 8.91 (s, IH), 8.71 (s, IH), 8.00 (s, IH), 2.75 (q, 2H), 1.31 (t, 3H). MS m/z calculated for (M + H)+ 152, found 152.

The chemical industry reduces the impact on the environment during synthesis 38940-62-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 874959-68-9, 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. 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride. A new synthetic method of this compound is introduced below.

Ethyl 5-amino-3-methylbenzofuran-2-carboxylate (0.23 g, 1.05 mmol), 5-bromopyridine-2-sulfonyl chloride (0.54 g, 2.10 mmol), potassium carbonate(0.29 g, 2.10 mmol) was added successively to 30 mL of dichloromethane, and the mixture was stirred overnight at room temperature, and potassium carbonate was filtered off, and the residue was purified by column chromatography to yield 0.43 g (yield: 93.3%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,874959-68-9, 5-Bromopyridine-2-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; You Qidong; Wei Jinlian; Jiang Zhengyu; Guo Xiaoke; Xu Xiaoli; Zhang Xiaojin; (44 pag.)CN107619384; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55304-75-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 2e1 (64 mg, 0.30 mmol), morpholine (0.027 mL, 0.31 mmol) and triethylamine (0.050 mL, 0.36 mmol) in DMF (1 mL) is stirred overnight at ambient temperature. The mixture is then diluted with EtOAc and successively washed with water (4×) and brine. The organic phase is dried with MgSO4, filtered and concentrated to afford intermediate 2e2.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine.

Reference:
Patent; Beaulieu, Pierre L.; Coulombe, Rene; Fazal, Gulrez; Goulet, Sylvie; Poirier, Martin; Rancourt, Jean; Stammers, Timothy; Thavonekham, Bounkham; US2008/45516; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem