Tag: M.W=300-400

Synthetic Route of 59020-10-9, 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.59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, molecular weight is 368.1447, as common compound, the synthetic route is as follows.

General procedure: 4.Aryl halide (0.5 mmol), base (1 mmol), CuI (20 mol %), alkylstannylpyridine(0.75 mmol), and catalyst (1 mol %) were dissolvedin DMF (2 mL) in a 10 mL vial and heated at a specific temperatureunder N2 for 12 h. After the reaction was complete, and thenquenched with water. The mixture was diluted with ethyl acetate(10 mL), filtered through a pad of Celite, and followed by extractionwith ethyl acetate for three times. The combined organic layer wasdried over anhydrous Na2SO4, filtered, and evaporated under reducedpressure. The residual was purified by flash chromatographyon silica gel (ethyl acetate/hexane) to give the desired product.3.12 1-[4-(Pyridin-3-yl)phenyl]ethanone (3la) 19 Yellow solid, mp 74-75 C; 1H NMR (400 MHz, CDCl3): delta=8.89 (s, 1H), 8.66 (s, 1H), 8.07 (d, J=7.96 Hz, 2H), 7.91 (d, J=7.52 Hz, 1H), 7.68 (d, J=7.92 Hz, 2H), 7.40-7.42 (m, 1H), 2.65 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=26.7, 123.7, 127.3, 129.1, 134.5, 135.4, 136.5, 142.3, 148.3, 149.3, 197.5; HRMS-ESI (m/z): [M+H]+ calcd for C13H12NO+: 198.0913, found: 198.0918.

The chemical industry reduces the impact on the environment during synthesis 59020-10-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (18.2 g, 59.2 mmol) in diethylether (200 mL), at -78 C in a 1L 3 neck RBF, was added n-butyl lithium (1.6 M in hexane, 44.5 mL, 71.1 mmol). The resulting solution was stirred at that temperature for 10 minutes and ethyl-N-Boc-(S)-pyroglutamate (16.75 g, 65.2 mmol) in diethylether (130 mL) was added slowly, and the resulting solution was stirred at that temperature for 1 h. The reaction was stopped by the addition of saturated NH4C1 solution (150 mL) and extracted with EtOAc (2 x 250 mL).The organic layer was washed with water (2 x 150 mL), dried over anhydrous Na2S04 and concentrated to yield ethyl (S)-2-((tert-butoxycarbonyl)amino)-5-(5-chloro-2- (trifluoromethyl)pyridin-4-yl)-5-oxopentanoate which was carried forward to the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-95-0, 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 193274-02-1 , The common heterocyclic compound, 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate, molecular formula is C19H25N3O3, 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.

Step D. 3a(R)-Benzyl-2-methyl-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (L)-tartrate To a 2 liter, round bottom flask, equipped with a mechanical stirrer, addition funnel, and a thermocouple was added, sequentially, 3a-(R,S)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared according to Step C, 51.5 g, 0.15 moles, 1.0 equivalents) and methylene chloride (515 ml, 10 volumes). The mixture was agitated to form a solution which was then cooled to an internal temperature of 0 C.-5 C. To the cooled mixture was added trifluoroacetic acid (TFA, 130 ml, 192 g, 1.68 moles, 11.2 eq., 2.5 volumes). The TFA was added via the addition funnel over 15 minutes while maintaining an internal temperature of 0 C.-5 C. The reaction mixture was warmed to about 20 C. over 3 hours and then the reaction mixture was cooled to 10 C.-15 C. To the cooled reaction mixture was added sodium carbonate (92 g, 0.868 moles) in water (920 mL) over 20 minutes. The pH was 7.5. The reaction mixture was transferred to a 2 liter separatory funnel and allowed to settle. The organic portion was decanted and the aqueous portion was extracted with methylene chloride (130 ml, 2.5 volumes). The combined organic portions were transferred back to the 2 liter reactor and to it was added L-tartaric acid (24.77 g, 0.165 moles, 1.1 equivalents) dissolved in acetone (354 ml, about 7 volumes) and water (44 mL, about 1 volume). The reaction mixture was agitated and heated at about 38 C. overnight. The resultant slurry was cooled to 0 C.-5 C., granulated for 1 hour, then filtered. The solids were washed with 100 ml of cold acetone and then dried in vacuo at 40 C.-50 C. for 16 hours to afford 51.86 g (87.9% yield) of the title compound of Step D.

The synthetic route of 193274-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Busch, Frank R; Chiu, Charles K; Meltz, Clifford N; Post, Ronald J; Rose, Peter R; US2002/2283; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79491-46-6, 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. 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine, molecular formula is C6H4Br2N2O3, 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.

5.43 3-Methoxy-5-nitropyridine-2,6-diamine (33) A solution of 32 (0.5 g, 1.6 mmol) in aqueous ammonia (15 M, 12 mL, 180 mmol) was heated at 90 C for 1 h in a microwave oven. The reaction mixture was cooled, the yellow solid was collected by filtration, washed with a small amount of water, and dried under vacuum to afford 33 (230 mg, 78%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6, 393 K) delta = 7.48 (s, 1H), 7.35 (br, 2H), 6.81 (br, 2H), 3.80 (s, 3H); MS ES+ve m/z 185 (M+H)+.

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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

To the stirred solution of (2,6-dibenzyloxy-3-bromo-pyridine) 43-1 (5 g, 13.50 mmol)in dry THF (30 mL), 2.5 M BuLi in Hexane (7.08 g, 20.26 mmol) was added at -78C under inertatmosphere and stirred for 1 hour at rt. After that, dry DMF (1.5 mL) was added to the reactionmixture dropwise at -78C and stirring was continued for further 2 hours at room temperature. After completion of reaction, as evidenced from TLC, reaction mixture was quenched withsaturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate.Combined organic layer was separated, dried over anhydrous sodium sulfate and concentratedunder vacuum. The crude reaction mass was purified by column chromatography to obtain5 desired compound 43-2 (2,6-dibenzyloxypyridine-3-carbaldehyde) (2.8 g, 8.77 mmol, 64.92%yield) as sticky solid. ES (M+H): 320.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Christoper, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; DUPLESSIS, Martin; CHEN, Chi-Li; (791 pag.)WO2018/237026; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 53710-18-2, name is 3,5-Diiodopyridine, molecular formula is C5H3I2N, 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. Recommanded Product: 3,5-Diiodopyridine

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel flash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g, 45%) as a light yellow solid. MS: 399.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 53710-18-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59020-10-9, 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.59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, molecular weight is 368.1447, as common compound, the synthetic route is as follows.

General procedure: 4.Aryl halide (0.5 mmol), base (1 mmol), CuI (20 mol %), alkylstannylpyridine(0.75 mmol), and catalyst (1 mol %) were dissolvedin DMF (2 mL) in a 10 mL vial and heated at a specific temperatureunder N2 for 12 h. After the reaction was complete, and thenquenched with water. The mixture was diluted with ethyl acetate(10 mL), filtered through a pad of Celite, and followed by extractionwith ethyl acetate for three times. The combined organic layer wasdried over anhydrous Na2SO4, filtered, and evaporated under reducedpressure. The residual was purified by flash chromatographyon silica gel (ethyl acetate/hexane) to give the desired product.3.12 1-[4-(Pyridin-3-yl)phenyl]ethanone (3la) 19 Yellow solid, mp 74-75 C; 1H NMR (400 MHz, CDCl3): delta=8.89 (s, 1H), 8.66 (s, 1H), 8.07 (d, J=7.96 Hz, 2H), 7.91 (d, J=7.52 Hz, 1H), 7.68 (d, J=7.92 Hz, 2H), 7.40-7.42 (m, 1H), 2.65 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=26.7, 123.7, 127.3, 129.1, 134.5, 135.4, 136.5, 142.3, 148.3, 149.3, 197.5; HRMS-ESI (m/z): [M+H]+ calcd for C13H12NO+: 198.0913, found: 198.0918.

The chemical industry reduces the impact on the environment during synthesis 59020-10-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (18.2 g, 59.2 mmol) in diethylether (200 mL), at -78 C in a 1L 3 neck RBF, was added n-butyl lithium (1.6 M in hexane, 44.5 mL, 71.1 mmol). The resulting solution was stirred at that temperature for 10 minutes and ethyl-N-Boc-(S)-pyroglutamate (16.75 g, 65.2 mmol) in diethylether (130 mL) was added slowly, and the resulting solution was stirred at that temperature for 1 h. The reaction was stopped by the addition of saturated NH4C1 solution (150 mL) and extracted with EtOAc (2 x 250 mL).The organic layer was washed with water (2 x 150 mL), dried over anhydrous Na2S04 and concentrated to yield ethyl (S)-2-((tert-butoxycarbonyl)amino)-5-(5-chloro-2- (trifluoromethyl)pyridin-4-yl)-5-oxopentanoate which was carried forward to the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-95-0, 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem