Day: May 24, 2021

Application of 136117-73-2, Adding some certain compound to certain chemical reactions, such as: 136117-73-2, name is Imidazo[1,2-a]pyridine-7-carbaldehyde,molecular formula is C8H6N2O, 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 136117-73-2.

1.2(2) Preparation of Intermediate To a solution of intermediate of example 1.2(1). (27.369 mmol) in THF dry (120 ml) was added at 0 C. cyclopropylmagnesium bromide in THF 0.5 M (41.053 mmol) under nitrogen atmosphere. The reaction was stirred at 0 C. for 2 hours. Then the reaction mixture was concentrated to dryness. The residue was diluted with ethyl acetate (80 ml) and a aqueous solution of ammonium chloride (40 ml). An extraction was performed with brine (40 ml). The water layer was again extracted with EtOAc (80 ml). The organic layers were collected, dried over Na2SO4, filtered and concentrated to dryness, yielding 5.5 g of intermediate shown, used crude in the next step.

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. 136117-73-2, Imidazo[1,2-a]pyridine-7-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2012/35171; (2012); 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.40296-46-6, name is Ethyl 4,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.0527, as common compound, the synthetic route is as follows.Product Details of 40296-46-6

Example IX Preparation of [(4,6-dichloropyridin-3-yl)methyl](methyl)-oxido lambda4-sulfanylidenecyanamide (9) To a stirred solution of ethyl 4,6-dichloronicotinate (8.8 g, 40 mmol) in anhydrous THF (75 mL) cooled in an ice-water bath was added in a dropwise fashion 1 M LiAlH4 solution in THF (25 mL, 25 mmol). During the addition, the temperature was not allowed to rise above 25 C. After the addition was over, the reaction was warmed to 40 C. for 15 min, cooled, then quenched by the successive dropwise addition of water (0.95 mL), 15% aqueous NaOH (0.95 mL) and water (1.85 mL). The mixture was filtered through celite and the filtrated was dried (MgSO4), passed through a short pad of silica gel and concentrated to give a red oil. Ether (100 mL) was added whereupon a gummy precipitate immediately appeared, which was removed by filtration. The ether solution was allowed to stand at room temperature overnight, during which time more precipitate was formed which was removed again by filtration. The ether solution was concentrated and dried to give 3.25 g of the product 2,4-dichloro-5-hydroxy-methylpyridine in 46% yield as a nearly colorless oily solid. 1H NMR (300 MHz, CDCl3) delta 8.5 (s, 1H), 7.4 (s, 1H), 4.8 (s, 2H), 2.7 (bs, 1H); GC-MS: mass calcd for C6H5Cl2NO [M]+, 177. Found

At the same time, in my other blogs, there are other synthetic methods of this type of compound,40296-46-6, Ethyl 4,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Zhu, Yuanming; Loso, Michael R.; Nugent, Benjamin M.; Huang, Jim X.; Rogers, Richard B.; US2008/108667; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 230301-11-8, tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, 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, Recommanded Product: tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, blongs to pyridine-derivatives compound. Recommanded Product: tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

To a stirred solution of tert-butyl 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate(1 g, 4.479 mmol, 1 equiv.) in MeCN(120 mL) was added NIS(1.11 g, 4.927 mmol, 1.1 equiv.) at room temperature. The resulting mixture was stirred for 4 h at 60 degrees C. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18, 330 g; Mobile Phase A: Water/0.05% TFA, Mobile Phase B: ACN; Flow rate: 80 mL/min; Gradient: 35%B to 55%B in 25 min; Detector, 220nm; Monitor,254 nm) to afford tert-butyl 3-iodo- 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate(390 mg, 24.94%) as a dark yellow solid

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine, 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, Computed Properties of C7H4BrIN2, blongs to pyridine-derivatives compound. Computed Properties of C7H4BrIN2

To a 500 ml 3-neck flask, 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (32 g, 99.1 mmol) and DMF (300 ml) were added. The solution was cooled to -40 C. under nitrogen and sodium hydride (2.8 g, 118.9 mmol) was added in 2 batches. The mixture was stirred at -40 C. for 1 hour. Then SEM-Cl (21 ml, 118.9 mmol) in DMF (50 ml) was added drop wise and the resulting mixture was allowed to stir at -40 C. for another 2 hours. The reaction was quenched with saturated NH4Cl (40 ml) and worked up with ethyl acetate, brine, dried with Na2SO4, concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 5-bromo-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (32.8 g, 73% yield). NMR (500 MHz, DMSO-d6) delta 0.06 (s, 9H), 0.91 (m, 2H), 3.62 (m, 2H), 5.70 (s, 2H), 8.04 (m, 1H), 8.11 (s, 1H), 8.51 (m, 1H). MS: m/z 455.9 (M+H+).

The synthetic route of 757978-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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. 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, 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.

4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in was dissolved in DMF (7.0 ml). After cooling to 0C, N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a darkbrown solid (455 mg). Physical properties: m/z[M+H]+ 279.1

According to the analysis of related databases, 60290-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SAGARA, Takeshi; ITO, Satoru; OTSUKI, Sachie; SOOTOME, Hiroshi; EP2657233; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 141-86-6, 2,6-Diaminopyridine, 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, Application In Synthesis of 2,6-Diaminopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Diaminopyridine

In a 100 mL three-necked round bottom flask, acetic anhydride (2.1 ml, 27.5 mmol) in 20 mL THF was added dropwise to a stirred mixture of pyridine-2,6-diamine (3.00 g, 27.5 mmol) and triethylamine (2.78 g, 27.5 mmol) in THF (40 ml) at 0C. After the reaction mixture was stirred at room temperature overnight, it was diluted with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine (2 x 1 OmL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether (10/i) to give the title compound as a solid. LCMS (ESI) calc?d for C7H9N30 [M+i ]: 152 found: 152; ?H NMR (300 MHz, CD3OD): oe7.38-7.32(m, 1H),718(d, J= 7.8 Hz, 1H), 6.24 (d,J= 8.1 Hz, 1H),2.08(s,3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,141-86-6, 2,6-Diaminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 733757-89-6, tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate, 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, 733757-89-6, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate

Description 21 : 6-methyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4- c] pyridineUnder an inert atmosphere of argon, LiAIH4 (2.3 M in THF; 7.5ml; 17.3mmol) was added dropwise over 2 minutes to a cool (O0C) stirring solution of 6-tert-butoxycarbonyl-3- (trifluoromethyl)-4,5,6,7-tetrahydro-1 H-pyrazolo[3,4-c]pyridine (2.0Og; 8.45mmol) in anhydrous THF (42ml). The resulting mixture was stirred in an oil bath at 580C for 17 hours, cooled to O0C, and quenched by the careful addition of an aqueous solution of sodium potassium tartrate (1 M; 50ml). After stirring at room temperature for 1 hour, the mixture was diluted with diethyl ether (50ml) and more aqueous sodium potassium tartrate (1 M; 50ml). After stirring at this temperature for a further 1 hour, the mixture was partitioned between water (100ml) and diethyl ether (200ml). The separated aqueous phase was extracted with ethyl acetate (200ml), and the combined organic phase was dried (MgSO4) and concentrated in vacuo. The resulting off-white solid (1.39g) was purified using an SCX column giving the title compound as a yellow solid (1.23g; 6.01 mmol)LC/MS (ES): Found 206 (ES+), retention time 1.81 mins. C8H10F3N3 requires 205.1 H-NMR (400MHz, CDCI3): 2.48 (3H, app s), 2.74 (4H, app s), 3.58 (2H, app s), 5.01(1 H, br s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,733757-89-6, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/113795; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine, 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, 757978-18-0, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

100 mL round bottom flaskIodo-1H-pyrrole [2,3-b] pyridine (M1) (100.0 mg, 3.1 mmol)20 mL of dichloromethane, triethylamine (930 mg, 9.2 mmol), DMAP (40 mg, 0.31 mmol),Benzenesulfonyl chloride (N1) (1100 mg, 6.2 mmol) was dissolved in 10 mL of dichloromethane under ice-cooling,Dropping funnel through the constant pressure drop into the solution, the drop is completed, stirring at room temperature 1h,TLC detection, no M1 remaining, washed 3 times, liquid separation, the organic phase anhydrous sodium sulfate drying,The solvent was removed by concentration and recrystallized from ethyl acetate (5 mL) to give a white solid which was dried to give 5-bromo-3-iodo-1- (phenylsulfonyl) -1H-pyrrole [2,3-b] pyridine (B8).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,757978-18-0, its application will become more common.

Reference:
Patent; Fudan University; Zhou, Yaming; Yang, Chengbin; Hong, Hui; Liu, Xiaofeng; Yang, Yongtai; Ling, Yun; Gu, Yu; Deng, Mingli; (38 pag.)CN106117181; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 118650-08-1, 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. 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate, molecular formula is C8H8BrNO2, 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-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 30 mg, 0.149 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (63 mg, 0.297 mmol) and water (0.2 mL) were added to a solution of (E)-1-(4-{1-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-3-ethyl-1-penten-3-ol (Example 38-(6); 50 mg, 0.099 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100C for 2.5 hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate = 1:1) to give the target compound as a colorless oil (12.5 mg, 24%). 1H-NMR (chloroform-d): 0.66 (6H, t, J=7.26Hz), 0.93 (6H, t, J=7.25Hz), 1.65 (4H, q, J=7.34Hz), 1.98 (6H, s), 2.11 (4H, q, J=7.42Hz), 2.35 (3H, s), 3.68 (2H, s), 3.72 (3H, s), 6.03 (1H, d, J=15.99Hz), 6.76 (1H, d, J=16.00Hz), 6.91 (2H, s), 6.97-7.01 (2H, m), 7.33 (1H, d, J=7.91Hz), 7.49 (1H, s), 8.35 (1H, d, J=2.14Hz), 8.47 (1H, d, J=2.14Hz).

According to the analysis of related databases, 118650-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); 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.100-55-0, name is 3-Pyridinemethanol, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.Computed Properties of C6H7NO

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5mol%), Bi(OTf)3 (0.05mol, 5mol%), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-55-0, 3-Pyridinemethanol, and friends who are interested can also refer to it.

Reference:
Article; Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; 52; (2017); p. 7301 – 7307;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem