Category: pyridine-derivatives

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.58584-63-7, name is (6-Methoxypyridin-3-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Quality Control of (6-Methoxypyridin-3-yl)methanol

To a stirred solution of (6-methoxypyridin-3-yl)methanol (49.8 mg, 0.358 mmol) in DMF (0.5 ml.) at 0 C was added sodium hydride (60% dispersion in mineral oil) (10.73 mg, 0.447 mmol) and the reaction mixture stirred for 15 min prior to the addition of 4- methylbenzene-l-sulfonyl chloride (85 mg, 0.447 mmol). The reaction was stirred for a further 30 min at this temperature. In a separate flask, 5-(4-chloro-lH-imidazol-2-yl)-l,3- dimethylpyridin-2(lH)-one (for an example preparation, see Intermediate 12, 40 mg, 0.179 mmol) was dissolved in DMF (0.5 ml.) at 0 C, to which sodium hydride (60% dispersion in mineral oil) (8.58 mg, 0.358 mmol) was added and the reaction stirred for a further 30 min. The solution containing the tosylated pyridine was added dropwise to the flask containing the imidazole, and the reaction stirred for a further 16 h. The solvent was removed in vacuo and the crude product was purified by MDAP (Method A) to afford the title compound as a colourless film (16 mg, 0.04 mmol, 23%). LCMS (System A): tRET = 0.79 min; MH+ 345.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-63-7, (6-Methoxypyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89937-77-9, 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 89937-77-9 as follows.

Step 1 4-Hydroxymethyl-1H-pyridin-2-one 2-Oxo-1,2-dihydropyridine-4-carboxylic acid methyl ester (1.8 g, 12.2 mmol), prepared as described in J. Org. Chem., 26, 428 (1961), was suspended in THF(100 ml). A small amount of DMF was added to help increase solubility. LiBH4 (61 mmol) was added and the reaction was stirred for 18 hours at room temperature. MeOH and H2 O are added to quench the reaction. The reaction is then concentrated to yield a yellow oil. Flash chromatography (5% MeOH/CHCl3 to 20% MeOH/CHCl3) yielded 4-hydroxymethyl-1H-pyridin-2-one as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.38-7.36 (1H,d); 6.56 (s, 1H); 6.37-6.36 (d, 1H); 4.50 s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89937-77-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6093737; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 6937-03-7, name is Methyl 2-aminoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H8N2O2

Methyl 2-aminopyridine-4-carboxylate (2 g, 13.14 mmo 1, 1.00 equiv) wasdissolved in tert-butano 1 (20 mL) after which di-tert-butyl dicarbonate (4.02 g, 18.42mmol, 1.40 equiv) was added. The reaction mixture was agitated at 60C overnight then the reaction was halted through the addition of an aqueous 1M NaHCO3 solution (50 mL). The solid was recovered by filtration, washed with 50 mL of EtOH then dried in vacuo to yield 2.5 g (75 %) of compound 2E in the form of a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 6937-03-7.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18615-86-6 ,Some common heterocyclic compound, 18615-86-6, molecular formula is C6H7NO, 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 1 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy)-2-methylpyridine 2-Methylpyridin-4-ol (60 mg, 0.55 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 mL), and potassium carbonate (75.5 mg, 0.55 mmol) and (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (150 mg, 0.37 mmol) were successively added to the reaction solution and stirred overnight at 60 C. The reaction solution was cooled and extracted with dichloromethane (30 mL). The organic layer was washed with water (10 mL*3), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure and then separated by column chromatography to give 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy)-2-methylpyridine 319 (80 mg, yield: 50%). MS m/z (ESI): 440.8 [M+1] 1H NMR (400 MHz, CDCl3) 8.31 (d, J=6.0 Hz, 1H), 6.67-6.64 (m, 1H), 4.91 (s, 1H), 4.63-4.60 (m, 2H), 4.10-3.88 (m, 3H), 3.53-3.45 (m, 2H), 2.54 (s, 3H), 2.46-1.56 (m, 18H), 1.55 (s, 3H), 1.39-1.27 (m, 3H), 0.81 (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,18615-86-6, its application will become more common.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (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. 54903-50-3, name is 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine, molecular formula is C7H9NS, 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. name: 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine

To a stuffing solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (5.6 g, 40.3 mmol), and Et3N (6.1 g, 60.4 mmol) in MeOH (100 mL) was added Boc2O (10.5g, 48.4 mmol) in 30 mm at 0 C. The mixture was stuffed at 20 C for 16 hours. The reaction mixture was concentrated after the starting material was consumed and the residue re-dissolved in DCM, the organic solution washed with water and aq. HC1 (0.5 M), the organic phases was dried and concentrated to give 8.9 g (yield: 92.4%) of tert-butyl 6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxylate as white solid. ?H NMR (400MHz, CDC13) (ppm): 7.14 (d, 1=5.0 Hz, 1H), 6.81 (d, 1=5.0 Hz, 1H), 4.52 (br. s, 2H), 3.75 (br. s, 2H), 2.87 (br. s, 2H), 1.51 (s, 9H). LCMS (mlz): 240.2 [M+H]

With the rapid development of chemical substances, we look forward to future research findings about 54903-50-3.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; SHAPIRO, Gideon; (393 pag.)WO2015/200677; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 875781-17-2 , The common heterocyclic compound, 875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H4BrN3, 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.

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine (99 mg, 0.5 mmol), bis(pinacolato)diboron (152mg, 0.6 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (36.5 mg, 0.05 mmol) and potassium acetate (98 mg, 1 mmol) in 1,4-dioxane (5 mL) was degassed and stirred at 100 C under Argon atmosphere for 3 hrs. To the reaction mixute was added compound 8b (100 mg, 0.31 mmol), potassium carbonate (276 mg, 2 mmol) and water (1 mL). The resulting mixture was degassed and stirred at 100 C under Argon atmosphere for 3 hrs. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol/ammonium water 600:10:1, v/v) to give the title compound 9i (50 mg, 28% yield for two steps) as a yellow solid.

The synthetic route of 875781-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Songwen; Han, Fangbin; Liu, Peng; Tao, Jing; Zhong, Xuechao; Liu, Xiujie; Yi, Chongqin; Xu, Heng; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 790 – 793;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 799293-83-7, 3-Bromothieno[3,2-c]pyridin-4(5H)-one, 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, Safety of 3-Bromothieno[3,2-c]pyridin-4(5H)-one, blongs to pyridine-derivatives compound. Safety of 3-Bromothieno[3,2-c]pyridin-4(5H)-one

Step-1: (0216) (0217) Preparation of 3-(4-chloro-3-(trifluoromethyl)phenyl)thieno[3,2-c]pyridin-4(5H)-one: (0218) [00115] To a solution of 3-bromothieno[3,2-c]pyridin-4(5H)-one (0.55 g, 2.17 mmol) and (4-chloro-3-(trifluoromethyl)phenyl)boronic acid (0.73 g, 3.25 mmol) in 1,4-dioxane:water mixture (20 mL, 4:1), potassium carbonate (0.9 g, 6.51 mmol) was added. The reaction mixture was purged with argon for 15 minutes and PdCl2(PPh3)2 (0.15 g, 0.21 mmol) was added. Then the reaction mixture was stirred at 100 C for 18 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel column chromatography using 30% ethyl acetate in hexane to afford the title compound 3-(4-chloro-3-(trifluoromethyl)phenyl)thieno[3,2-c]pyridin-4(5H)- one (0.74 g, 94% yield) as off-white solid. Calculated (M+H): 330; Found (M+H): 330.0.

The synthetic route of 799293-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); 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.88912-27-0, name is 3-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.Product Details of 88912-27-0

A mixture of 0.35 g of 2-amino-4-trifluoromethoxy phenol, 0.29 g of 3- chloroisonicotinic acid, 1.04 g of (benzotriazole-l-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (hereinafter, referred to as a BOP reagent), 0.24 g of triethylamine and 5 ml of DMF was stirred at room temperature for two hours. Water was added to the reaction mixture, precipitated solid was collected by filtration. The resultant solid was dissolved in ethyl acetate. Then, the organic layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was subjected to silica gel column chromatography to give 0.43 g of 3-chloro- N-[2-hydroxy-5-(trifluoromethoxy)phenyl]isonicotinamide.-NMR (DMSO-d6) delta: 10.37 (br s, 1H), 10.15 (br s, 1H), 8.75-8.73 (m, 1H), 8.64-8.61 (m, 1H), 8.04-8.01 (m, 1H), 7.63-7.60 (m, 1H), 7.07-7.02 (m, 1H), 6.98-6.94 (m, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-27-0, 3-Chloroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49220; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 107504-08-5, Adding some certain compound to certain chemical reactions, such as: 107504-08-5, name is 5-Fluoro-2-picolinic acid,molecular formula is C6H4FNO2, 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 107504-08-5.

In the ice bath,To a solution of 5-fluoro-2-pyridinecarboxylic acid (10 g) in methanol was slowly added dropwise thionyl chloride (10.3 mL).Dripping is completed.After moving to 80C for 8 hours,Cool to room temperatureMethanol was distilled off under reduced pressure.Diluted with ethyl acetate,In the ice bath,Saturated sodium bicarbonate solution was added to the reaction mixture,Adjust pH = 8 or so.Extract with ethyl acetate,The combined organic phases are washed with saturated brine,Dried over anhydrous sodium sulfate,Filter and concentrate the filtrate in vacuoThe residue was separated by silica gel column chromatography to give the title compound (9.895 g).

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. 107504-08-5, 5-Fluoro-2-picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (2018); A;,
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.96568-04-6, name is Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, molecular formula is C10H8Cl2FNO3, molecular weight is 280.08, as common compound, the synthetic route is as follows.Safety of Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate

Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (19.5 g, 69.6 mmol) and triethyl orthoformate (23.1 ml, 140 mmol) were initially charged in acetic anhydride (46 ml, 490 mmol) and the mixture was stirred at 140 C. overnight. The reaction mixture was then concentrated under reduced pressure and reacted further in the subsequent steps without further work-up. Quantitative conversion was assumed. LC-MS (Method 1): Rt=1.00 min; MS (ESIpos): m/z=336 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96568-04-6, Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; VAKALOPOULOS, Alexandros; BOULTADAKIS ARAPINIS, Melissa; STRAUB, Alexander; TINEL, Hanna; BRECHMANN, Markus; WITTWER, Matthias Beat; KULLMANN, Maximilian Andreas; FREUDENBERGER, Till; MONDRITZKI, Thomas; MARQUARDT, Tobias; (165 pag.)US2019/263805; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem