Category: pyridine-derivatives

Electric Literature of 13445-16-4 , The common heterocyclic compound, 13445-16-4, name is 3-Bromo-2,6-dimethoxypyridine, molecular formula is C7H8BrNO2, 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 2: Preparation of (3aR,4R,6S,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2,6- dimethoxypyridin-3-yl)-2,2-dimethyltetrahydro-3aH-[l,3]dioxolo[4,5-c] (17d) To a stirred solution of 3-bromo-2,6-dimethoxypyridine (17b) (2.73 g, 12.50 mmol) in Tetrahydrofuran (30 mL) was added n-Butyl lithium (1.6 M solution in hexanes, 7.81 mL, 12.50 mmol) at -78 C and stirred at the same temperature for 1 hr. To the anion formed at – 78 C was added a freshly prepared solution of (3aR,4R,6aS)-4-((tert- butyldimethylsilyloxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[l,3]dioxolo[4,5-c]pyrrole (lk) (2.85 g, 10 mmol) in toluene (1.2 molar solution) over a period of 15 minutes. The reaction stirred for 30 minutes at -78 C, quenched with water (50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water (50 mL), brine (50 mL) dried, filtered and concentrated in vacuum. The crude residue was purified by flash column chromatography (silica gel 40 g, eluting with 0-100% ethyl acetate in hexanes) to afford (3aR,4R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-6-(2,6-dimethoxypyridin-3- yl)-2,2-dimethyltetrahydro-3aH-[l,3]dioxolo[4,5-c]pyrrole (17d) (1.35 g, 31.8 % yield) as a light brown syrup. 1H NMR (300 MHz, DMSO-d6) delta 7.64 (d, J = 8.1 Hz, 1H), 6.29 (d, J = 8.0 Hz, 1H), 4.42 – 4.28 (m, 2H), 4.09 (d, J = 4.3 Hz, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.57 (d, J = 5.0 Hz, 2H), 3.05 (d, J = 4.8 Hz, 1H), 2.85 (s, 1H, D20 exchangeable), 1.40 (s, 3H), 1.17 (s, 3H), 0.82 (s, 9H), -0.00 (d, J= 1.3 Hz, 6H). Mass spec (ES+) 425.1 (M+l).

The synthetic route of 13445-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; BANTIA, Shanta; WU, Minwan; KUMAR, V., Satish; WO2014/78778; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83393-46-8, Adding some certain compound to certain chemical reactions, such as: 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone,molecular formula is C9H8N2O, 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 83393-46-8.

A solution of 6.89 g (43.0 mmol) of 1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone in 50 ml of DMF is added dropwise under nitrogen to a suspension of 1.25 g (52.0 mmol) of sodium hydride in 100 ml of DMF. The mixture is stirred at room temperature for one hour and then cooled to 0. A solution of 9.92 g (52.0 mmol) of toluene-4-sulfonyl chloride in 50 ml of DMF is added dropwise, and the reaction mixture is stirred at 0 for 2 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is dried over sodium sulfate, evaporated, and the residue is stirred with water. The residue is filtered off with suction and dried in vacuo: 1-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanone as colourless crystals; ESI 315, m.p. 187-189.

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. 83393-46-8, 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dorsch, Dieter; Sirrenberg, Christian; Mueller, Thomas; US2010/173923; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, 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, 936011-17-5, blongs to pyridine-derivatives compound. Safety of 5-Bromo-2-methoxyisonicotinaldehyde

To a solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (23.5 g, 108.8 mmol) in MeOH (100 mL) were successively added a solution of I2 (35.9 mg, 141.4 mmol) in MeOH (75 mL) and a solution of KOH (15.9 g, 282.8 mmol) in MeOH (75 mL) at 0 C. The resulting mixture was stirred for 1 hr at 0 C and the reaction was quenched with saturated aqueous NaHS03. The resulting mixture was diluted with DCM (400 mL). The separated organic phase was washed with H20 (150 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column (eluting with PE_EA=20: 1, v:v) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (14.9 g) as a light yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936011-17-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17075-15-9, 4-(Methylsulfonyl)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, 17075-15-9, blongs to pyridine-derivatives compound. HPLC of Formula: C6H7NO2S

EXAMPLE 1A 4-[2-[4-[4-(trifluoromethyl)phenoxy]phenyl]ethoxy]pyridine (Compound 1A) To a suspension of 0.2 g of 60% NaH (as an oil dispersion, 0.005 m) in 5 mL of DMF was added 1.41 g (0.005 m) of 2-[4-[4-(trifluoromethyl)phenoxy]phenyl]ethanol. The mixture was stirred at room temperature for 30 minutes, until hydrogen evolution ceased. To the mixture was then added 0.79 g (0.005 m) of 4-(methylsulfonyl)pyridine, and the mixture was stirred overnight at room temperature. Excess DMF was then removed in vacuo. The resulting material was diluted with water, and the product was extracted into CH2 Cl2. The CH2 Cl2 layer was separated and filtered through phase separating paper, then concentrated. The residue was adsorbed onto silica gel and chromatographed, eluding with CH2 Cl2 ?30% EtOAc/CH2 Cl2. The resulting material was rechromatographed over fine-particle silica gel, eluding with CH2 Cl2 ?50% EtOAc/CH2 Cl2. Yield 0.5 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17075-15-9, its application will become more common.

Reference:
Patent; DowElanco; US5399564; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, 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.

Step B: 6-chloro-4-methoxypyridine-3 -carbonitrile: A solution of 5 -bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 mm. Atthis point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate/hexane to afford the product.

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 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP; TANG, Haifeng; PIO, Barbara; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; FERGUSON, Ronald Dale, II; GUO, Zack Zhiqiang; CHOBANIAN, Harry; FRIE, Jessica; GUO, Yan; WU, Zhicai; YU, Yang; WANG, Ming; WO2015/17305; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19230-55-8 ,Some common heterocyclic compound, 19230-55-8, molecular formula is C6H6ClN, 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.

EXAMPLE 81 COMPOUND 81: N1-(3-chloro-5-methyl-pyridin-2-ylmethyl)-N1-(3-isopropyl-pyridin-2-ylmethyl)-butane-1,4-diamine (HBr salt) At -78 C., under N2, BuLi (2.5 M in hexanes, 0.80 mL, 2.0 mmol) was added to a solution of TMEDA (0.30 mL, 2.0 mmol) in dry Et2O (20 mL). After addition the mixture was warmed to room temperature. After stirred at room temperature for 30 min the mixture was cooled to -78 C., and added to a solution of 3-chloro-5-methyl-pyridine (0.255 g, 2.00 mmol) (Bushby et al. J. Chem. Soc. Perkin Trans. 11978, 1578) in dry Et2O (10 mL) pre-cooled at -78 C. The mixture was stirred at -78 C. for 30 min and then warmed to room temperature for 1 h. Water (15 mL) was added, and the mixture was extracted with Et2O (3*40 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (CH2Cl2) to afford 3-chloro-5-methyl-pyridine-2-carbaldehyde (0.096 g, 31%). 1H NMR (CDCl3) delta 2.44 (s, 3H), 7.65 (s, 1H), 8.54 (s, 1H), 10.28 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19230-55-8, its application will become more common.

Reference:
Patent; Bridger, Gary; McEachern, Ernest J.; Skerlj, Renato; Schols, Dominique; US2004/209921; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84487-03-6, 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. 84487-03-6, name is 6-Chloro-5-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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.

A mixture of 6-chloro-5-nitropyridin-2-amine(0.26 g, 1.50 mmol), benzylmercaptan (0.19mL, 1.65 mmol), K2CO3 (0.25 g, 1.83 mmol) and DMF (2.1 mL) was stirred at 80 C for 3.5 h. The mixture was poured into water and extracted with CH2CI2 (3×15 mL). The combined organic layers were dried over anhydrous Na2S04 and concentrated. The residue was dissolved in CH2CI2, and the product was precipitated by addition of hexane to give the sub-title compound (0.32 g, 83 %).

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 84487-03-6, 6-Chloro-5-nitropyridin-2-amine.

Reference:
Patent; OBLIQUE THERAPEUTICS AB; PELCMAN, Benjamin; SUNA, Edgars; STAFFORD, William; PRIEDE, Martins; (90 pag.)WO2018/146472; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 121643-44-5, 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 121643-44-5 as follows.

Preparation Example 36 2-Methoxy-3-(trifluoromethyl)pyridine (8 g), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (17 g), and trifluoroacetic acid (32 mL) were mixed, followed by stirring at room temperature for 22 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added diisopropyl ether. The precipitated solid was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine (9.4 g) as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; KOIKE, Takanori; NEGORO, Kenji; TANAKA, Hiroaki; MAEDA, Jun; YOKOYAMA, Kazuhiro; TAKAMATSU, Hajime; (146 pag.)EP3153511; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89364-04-5 , The common heterocyclic compound, 89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, 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.

After the phenoxazine 20.0g (109.16mmol), 3-Bromo-4-nitro-pyridine 25.21 g (120.08mmol), the NaO (t-Bu) 15.73 g (163.75 mmol), the Pd 2 (dba) 3 2.99 g (3.27 mmmol) was suspended in the toluene 436 mL P (t-Bu) 31.58 mL (6.55 mmol) was put and it mixed reflux underthe nitrogen air current for 24 hours. It extracts in thedichloromethane and distilled water and the organic layer the silica gel is filtered. Hexane the organic solution is removed: it recrystallized as the dichloromethane andethyl acetate and it obtained the intermediate product(I) 23.33 g (yield : 70 %) by the dichloromethane = 7 :3 (v/v) after the silica gel column.

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheil Industries Co., Ltd.; Jang, Yuna; Hong, Jin Suk; Kang, Dong Min; Sin, Ji Hun; Yu, Dong Gyu; Yu, Uhn Sun; Lee, Byung Kwan; Lee, Sang Sin; Lee, Han Ir; Jung, Su Young; Han, Su Jin; (34 pag.)KR2015/41508; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 77837-09-3, Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-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, SDS of cas: 77837-09-3, blongs to pyridine-derivatives compound. SDS of cas: 77837-09-3

6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid: Lithium hydroxide monohydrate (0.366 g, 8.73 mmol) was added to a mixture of methyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate (1.0 g, 4.37 mmol), tetrahydrofuran (9 mL) and water (6 mL) at 0° C. The mixture was stirred for 1 hour, diluted with water and washed with ethyl acetate. The pH of the aqueous layer was adjusted to 2 using 2 N hydrochloric acid and the precipitate was filtered to give the title compound as a brown solid (0.740 g, 79percent). m.p. 256-263° C.; 1H NMR (400 MHz, DMSO-d6) delta 6.53 (d, J=9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, J=2.5, 9.8 Hz, 1H), 8.23 (d, J=2.5 Hz, 1H); IR (KBr) nu 3446, 1708, 1645, 1577, 1263, 1228 cm-1; MS 214 (M-1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,77837-09-3, Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/319026; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem