Category: pyridine-derivatives

Synthetic Route of 183208-34-6 ,Some common heterocyclic compound, 183208-34-6, molecular formula is C7H5BrN2O, 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.

To a mixture of 5-bromo-7-azaoxindole (213 mg, 1 mmol) in dimethylsulfoxide (1 ml) and ethanol (5 ml) in Parr bomb were added triethylamine (0.31 ml, 2.25 mmol), palladium acetate (33.7 mg, 0.15 mmol), and 1,3-(bisdiphenylphosphino)propane (61.9 mg, 0.15 mmol). Carbon monoxide gas (40 atm) was applied and the reaction mixture was heated at 95 C. for 18 hours with vigorously stirring. The reaction mixture was diluted with diethyl ether (50 ml) and washed with water (10 ml). The aqueous layer was thoroughly extracted with diethyl ether. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituation of the crude product with methanol yielded 5-(carboethoxy)-7-azaoxindole as a tan solid (53 mg, 25.7%). 1H NMR (DMSO-d6): delta 11.39 (s, 1H), 8.62 (s, 1H), 7.95 (s, 1H), 4.27 (q, 2H, J=7 Hz), 3.59 (s, 2H), 1.28 (t, 3H, J=7 Hz). MS (-ve APCl): 205 (4, M-H).

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. 183208-34-6, 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1060808-94-7, 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. 1060808-94-7, name is 6-Amino-4-chloronicotinic acid. A new synthetic method of this compound is introduced below.

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide methyl iodide (0.175 g, 0.630 mmol) and 1-hydroxybenzotriazole monohydrate (0.097 g, 0.630 mmol) were added to a stirred solution of compound 32 (0.072 g, 0.420 mmol) in DMF (2 mL) at room temperature. After 15 min, m-toluidine (77 muL, 0.714 mmol) was added and the reaction mixture stirred at room temperature for 18 h. The reaction mixture was poured onto water (5 mL) and extracted with EtOAc (2 × 10 mL). The combined extracts were washed successively with saturated sodium bicarbonate solution (10 mL), water (3 × 10 mL), and brine (10 mL), dried (MgSO4) and concentrated to give the crude 3-carboxamido-4-anilino intermediate as a brown gum. This was taken up in 1,4-dioxane (2 mL), treated with ethyl isocyanate (23 muL, 0.300 mmol) and heated to 80 C for 18 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (5 mL) and reduced in vacuo directly onto SiO2. Column chromatography (SiO2), eluting with 2:1 Petrol-EtOAc to neat EtOAc, afforded the title compound (0.029 g, 0.072 mmol, 17%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060808-94-7, its application will become more common.

Reference:
Article; Yule, Ian A.; Czaplewski, Lloyd G.; Pommier, Stephanie; Davies, David T.; Narramore, Sarah K.; Fishwick, Colin W.G.; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 31 – 38;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 52311-50-9, 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 52311-50-9, name is 2-Chloro-4-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 2-chloro-4-ethoxypyridine (13 g, 82 mmol) and H2SO4 (40 mL, 750 mmol) was added NBS (17.62 g, 99 mmol). Then the mixture was stirred at 60 C for 10 h. After cooling to rt, the mixture was poured into cold water (300 mL). The mixture was extracted with EA (200 mL x 2). The combined organic layer was washed with saturated NaHCC>3 solution (200 mL x2) and concentrated. The crude material was purified by silica column chromatography (PE/EA = 15: 1). All fractions found to contain product by TLC (PE/EA = 5: 1, Rf = 0.6) were combined and concentrated to yield a yellow solid of 5-bromo-2-chloro-4-ethoxypyridine (8.5 g, 26.3 mmol, 32% yield): NMR (400 MHz, CDC13) delta 8.32 (s, 1H), 6.79 (s, 1H), 4.16 (q, J= 6.8 Hz, 2H), 1.50 (t, J = 6.8 Hz, 3H); ES-LCMS m/z 238 (M+3).

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 52311-50-9, 2-Chloro-4-ethoxypyridine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EIDAM, Hilary Schenck; DEMARTINO, Michael P.; GONG, Zhen; GUAN, Amy Huiping; RAHA, Kaushik; WU, Chengde; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; CHEUNG, Mui; WO2014/141187; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19230-55-8 , The common heterocyclic compound, 19230-55-8, name is 3-Chloro-5-methylpyridine, 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.

General procedure: 2 mol% Pd(OAc)2/3 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 45 C under an argon atmosphere for 1h to be a dark brown solution. 1 mol% CuI/1.1 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 60 C under an argon atmosphere for 2h to be a colorless transparent solution. The amount of catalyst and solvent should scaled up by the number of reactions. Benzoxazoles (0.25 mmol), aryl chlorides (0.3 mmol) and K3PO4*7H2O (42.3 mg, 0.125 mmol, 0.5 equiv) were added to an oven-dried 10 ml reaction vial equipped with a stir bar. A stock solution of Pd(OAc)2/Nixantphos and CuI/Nixantphos in 1 ml of dry DMF was taken up by syringe and added to the reaction vial. The reaction vial filled with argon was then sealed with a septum. The reaction mixture was stirred for12 h or 24 h at 120 C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash chromatography.

The synthetic route of 19230-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Ling-Li; Yin, Bo; Tian, Xing-Chuan; Yuan, Ming-Yong; Li, Xiao-Huan; Gao, Feng; Tetrahedron Letters; vol. 60; 51; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71670-70-7 , The common heterocyclic compound, 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, molecular formula is C7H9Cl2N, 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.

Using 2-chloromethyl-5-methylpyridine hydrochloride (170 g) and thiourea (86 g) as the starting materials, 2-(5-methylpyrid-2-ylmethyl)isothiourea dihydrochloride (160 g) is obtained. 2-Chloromethyl-5-methylpyridine hydrochloride can be prepared in accordance with the method described by R. Nicoletti and M. L. Forcellese, Gazz. Chim. Ital., 97, 148 (1967).

The synthetic route of 71670-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Industries; US4272534; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1192813-41-4, 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 1192813-41-4 as follows.

Step-2 -Preparation of 6-(difluoromethoxy)pyridin-3-amine To a solution of 2-(difluoromethoxy)-5-nitropyridine (0.900 g, 2.35 mmol) in ethanol (5.0 mL), was added iron powder (0.400 g, 7.14 mmol) and conc. HCl (0.2 mL). The reaction mass was refluxed for 1/2 h. Ethanol was removed under vacuum. To the reaction mass, water was added, basified with NaHCO3 and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.400 g of the desired product. 1HNMR (DMSO-d6): delta 7.65 (s, 1H), 7.52-7.03 (t, J=72.0 Hz, 1H), 7.27 (s, 1H), 6.73 (d, J=8.4 Hz, 1H); MS [M-H]-: 159.14.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1192813-41-4, its application will become more common.

Reference:
Patent; Glenmark Pharmaceuticals S.A.; US2012/108583; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. A new synthetic method of this compound is introduced below., Quality Control of (E)-3-(6-Aminopyridin-3-yl)acrylic acid

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3-(6-AMINO-PYRIDIN-3- yl) acrylic acid (164 mg, 1.0 mmol), (2-ethoxy-3-methoxy-benzyl) methylamine (215 mg, 1.1 mmol), HOT HO (149 mg, 1.1 mmol) and DIPEA (525 1L, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The organic layer was washed with brine (2×30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2CL2) furnished pure free base which was dissolved in CH2CL2 (10 mL). After addition of HCl (1.5 mL, 1M in ether), the solvents were evaporated and the residue was washed with ether and dried to afford the title compound (172 mg, 46%). 1H NMR (300 MHz, DMSO-d6) 8 8.28 (m, 3H), 7.48 and 7.45 (rotamers, 2d, J= 15.4 Hz, 1H), 7.25 and 7.23 (rotamers, 2d, J= 15.4 Hz, 1H), 7.00 (m, 3H), 6.62 (m, 1H), 4.78 and 4.63 (rotamers, 2s, 2H), 3.98 (m, 2H), 3.79 (s, 3H), 3.08 and 2.84 (rotamers, 2s, 3H), 1.28 (m, 3H). MS (ESI) mle 342 (M+H) +.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113293-70-2, 2,6-Dichloroisonicotinaldehyde, 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, 113293-70-2, blongs to pyridine-derivatives compound. Product Details of 113293-70-2

Step 23a: tert-butyl 4-((2,6-dichloropyridin-4-yl)methyl)piperazine-1-carboxylate (Intermediate 23a) 2,6-dichloroisonicotinaldehyde (106 mg, 0.6 mmol), N-Boc-piperizane (112 mg, 0.6 mmol) and 320 mg of NaBH(OAc)3 powder was stirred in 5 mL of dichloromethane at room temperature for 1 hr. 3 mL of saturated NaHCO3 aqueous solution was added, the reaction mixture was stirred for additional 30 min. After regular aqueous workup with dichloromethane-water, the reaction mixture was subject to column chromatography on silica gel, eluting with heptane/ethyl acetate (v/v 3/1), giving 150 mg of desired product as colorless oil. MS: m/z 346.0 (ES+); 290.0 (M-Bu-t, ES+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; AVILA THERAPEUTICS, INC.; US2011/230476; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below., Safety of 6-Chloro-2-methyl-3-nitropyridine

6-methoxy-3-nitro-2-picoline 0.46 gm (20 mMol) sodium were dissolved in 15 mL anhydrous methanol. To this solution were added 2.3 gm 6-chloro-3-nitro-2-picoline in portions. The resulting mixture was stirred for 18 hours at room temperature and then 1 hour at reflux. The reaction mixture was poured into 100 mL of ice water with vigorous stirring. The suspension was filtered and the solid dried at 30 C. under reduced pressure for 18 hours to provide 2.04 gm (91%) of the desired compound as a tan solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22280-60-0, 6-Chloro-2-methyl-3-nitropyridine.

Reference:
Patent; Eli Lilly and Company; US5874427; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 944900-06-5 ,Some common heterocyclic compound, 944900-06-5, molecular formula is C7H3ClF3NO, 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.

2-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 8 (11.96 g, 57.1 mmol) was added to a solution of N-Boc ethylenediamine (5.83 mL, 58.2 mmol) and Na2SO4 (50 g) in CH2Cl2 (400 mL) at room temperature, and the reaction mixture was stirred for 17 h. After the reaction mixture was concentrated, the residue was purified by silica gel column chromatography (hexane/AcOEt = 3:2) to provide the imine (13.87 g, 69%) as a yellow oil. 1H NMR (CDCl3) delta: 8.67 (1H, s), 8.53 (1H, d, J = 7.8 Hz), 7.68 (1H, d, J = 7.8 Hz), 4.79 (1H, br s), 3.83 (2H, t, J = 5.5 Hz), 3.50 (2H, q, J = 5.7 Hz), 1.44 (9H, s). A solution of allylmagnesium bromide in Et2O (0.7 M, 60 mL, 42 mmol) was added to a solution of the imine (13.44 g, 38.2 mmol) in THF (150 mL) under N2 atmosphere at 0 C, and the mixture was stirred at the same temperature for 45 min. Then, the reaction mixture was diluted with H2O (200 mL), extracted with AcOEt (400 mL), washed with brine, dried (Na2SO4), concentrated. The residue was purified by silica gel column chromatography (hexane/AcOEt = 7:3) to provide 9 (10.91 g, 73%) as a yellow oil. 1H NMR (CDCl3) delta: 8.12 (1H, d, J = 8.2 Hz), 7.64 (1H, d, J = 7.8 Hz), 5.82-5.71 (1H, m), 5.17-5.11 (2H, m), 4.72 (1H, br s), 4.21-4.10 (2H, m), 3.21-3.14 (2H, m), 2.65-2.59 (1H, m), 2.57-2.52 (1H, m), 2.47-2.41 (1H, m), 2.24-2.16 (1H, m), 1.44 (9H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,944900-06-5, its application will become more common.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Ichikawa, Masanori; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Kimura, Takako; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 89 – 104;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem