Pyridine-derivatives

Electric Literature of 1042141-37-6, 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.1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate, molecular formula is C9H7BrN2O2, molecular weight is 255.07, as common compound, the synthetic route is as follows.

A mixture of methyl S-bromo-lJ-diazabicyclo^.S.Ojnona^^ojS-tetraene-S-carboxylate (0.65 mmol, 165 mg), tert-but5d N-methyl-N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-yl]carbamate (0.98 mmol, 312 mg), Pd(dprhof)Cl2*DCM (65 mumol, 53mg) and cesium carbonate (1.95 mmol, 656 mg) in DMF (5 mL) was heated at 80 CC under an argon atmosphere for 1 h. The reaction mixture was filtered and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (EtOAc / hep) to give 150 mg of methyl 2-[6-[methyl-[(2-methylpropan- 2-yl)oxycarbonyl]amino]pyridin-3-yl]imidazo[2,l-fJpyridine-6-carboxylate as a yellow solid. MS m/z (M+H) 383

The chemical industry reduces the impact on the environment during synthesis 1042141-37-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 121643-44-5, 2-Methoxy-3-(trifluoromethyl)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, 121643-44-5, blongs to pyridine-derivatives compound. COA of Formula: C7H6F3NO

Intermediate 1 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 113.0 mmol) and 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18 h under argon. The TFA was removed in vacuo (50 mbar, 45 C.) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL). The filtrate was concentrated in vacuo, diluted with heptane/tert-butyl methyl ether (5/1, 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane/EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHCO3 (20 g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5 g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1H) 8.4 (d, 1H).

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; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129432-25-3, 2,6-Dichloro-4-methylpyridin-3-amine, 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, 129432-25-3, blongs to pyridine-derivatives compound. SDS of cas: 129432-25-3

To a mixture of 2,6-dichloro-4-methylpyridin-3-amine (0.500 g, 2.82 mmol) and potassium thiocyanate (0.823 g, 8.47 mmol) in ethanol (7.5 mL) at rt was added concentrated hydrochloric acid (10.04 mL, 330 mmol) dropwise. The mixture was heated at 100 C for 44 h. Additional potassium thiocyanate (0.823 g, 8.47 mmol) was added and the mixture was heated at 100 C for additional 31 h. The reaction mixture was concentrated under vacuum to dryness. To the residue was added 1 N NaOH solution (10 mL), followed by solid K2CO3, until the mixture became basic (pH = 9-10). The mixture was extracted with dichloromethane (4 x 40 mL). The combined extracts were dried over anhydrous Na2S04, filtered, and concentrated under vacuum. The residue was purified by flash chromatograph (80 g silica gel, solid loading, 0-6% methanol/dichloromethane) to provide 5-chloro-7-methylthiazolo[5,4-b]pyridin-2-amine (0.331 g, 1.658 mmol, 58.7 % yield) as a tan solid. MS (ESI) m/z: 199.9 [M+H]+; NMR (500 MHz, DMSO-de) delta 7.90 (s, 2H), 7.22 (s, 1H), 2.41 (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,129432-25-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FENG, Jianxin; LIU, Chunjian; HUANG, Yanting; (130 pag.)WO2019/89665; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, 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, Formula: C5H3Cl2N3O2, blongs to pyridine-derivatives compound. Formula: C5H3Cl2N3O2

Step B. 2,6-Dichloro-pyridine-3,4-diamineTo a solution of 2,6-dichloro-3-nitro-pyridin-4-amine (2.6 g, 14.4 mmol) from Step A in MeOH (150 mL) was added Raney Nickel catalyst (2 g) and the reaction agitated under a hydrogen atmosphere in a Parr apparatus (35 p.s.i.) for 2 h . The reaction mixture was filtered through a pad of Celite and concentrated to yield the title compound. MS: m/z – 178 (M + 1).

The synthetic route of 2897-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/153852; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 145335-90-6, name is Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride, the common compound, a new synthetic route is introduced below. Safety of Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride

Step B: Preparation of Imidazo[l,2-alpha]pyridine-2-carbonyl chloride Hydrochloride. Method 1: To imidazo[l,2-alpha]pyridine-8-carboxylic acid hydrochloride (10.0 g, 50.4 mmol), thionyl chloride (98 g, 60 mL, 822 mmol) was added. To the resulting mixture N,N- dimethylformamide (1.6 mL) was added. Gas evolution was noticed and the reaction mixture was heated to 50 0C overnight (18 h). The reaction mixture was then cooled to room temperature and the product was filtered and washed with isopropyl acetate (40 mL) followed by 10% isopropanol in isopropyl acetate (40 mL). The white solid thus obtained was dried under reduced pressure to afford the title compound (10.2 g, 93%). The compound was used without further purification in Step E.

The synthetic route of 145335-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
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.103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.Safety of 5-Bromo-2-methoxynicotinaldehyde

(5-bromo-2-methoxypyridin-3-yl)methanol 5-Bromo-2-methoxynicotinaldehyde (2 g, 9.26 mmol) was suspended in methanol (40 mL) and cooled to 0 C. Sodium borohydride (0.350 g, 9.26 mmol) was added, causing bubbling. The reaction mixture was stirred at 0 C. for 15 minutes, the flask was removed from the ice bath, and the mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was concentrated, and the crude material was taken up in methyl tert-butyl ether and saturated aqueous sodium bicarbonate. The phases were separated, and the organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (1.876 g, 8.60 mmol, 93% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.15 (d, J=2.5 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 4.66 (d, J=6.2 Hz, 2H), 3.99 (s, 3H), 2.15 (t, J=6.3 Hz, 1H); MS (DCI+) m/z 217.8 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 136888-17-0, 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. 136888-17-0, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridin-2(3H)-one, molecular formula is C7H5ClN2O, 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.

C. 5-Chloro-3-(2-thenoyl)-6-azaoxindole Pellets of sodium metal (232 mg, 10 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-chloro-6-azaoxindole (340 mg, 2.0 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.54 mL, 4.0 mmol). The mixture was heated under nitrogen at reflux overnight during which a precipitate formed. The mixture was cooled, poured into ice/water and acidified to pH 4 with 6N HCl solution. The solid product (475 mg) was collected by filtration, washed with water, and dried in the air. This material was recrystallized from methanol to afford the title compound (190 mg, 34%). 1 H NMR (DMSO-d6): delta10.62 (br s, 1H), 8.79 (d, J=3.2 Hz, 1H), 7.92 (s, 1H), 7.77 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.17-7.14 (m, 1H).

According to the analysis of related databases, 136888-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US5811432; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60010-03-9, 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 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 2,6-dichloro-4-methyl-3-nitropyridine (300 mg, 1.449 mmol) and sodium bicarbonate (243 mg, 2.90 mmol) in Tetrahydrofuran (THF) (20 mL)) was added (S)-dimethyl 2-aminosuccinate hydrochloride (430 mg, 2.174 mmol) at 0 C. under nitrogen. Then the reaction mixture was stirred at 65 C. for 24 hr. The reaction was monitored by TLC. The reaction mass filtered and washed with EtOAc (2×30 mL). The filtrate was concentrated under reduced pressure to give the crude material. The crude product was added to a neutral alumina column and was eluted with Hex/EtOAc (9:1). Collected fractions were concentrated under reduced pressure to afford the desired product (250 mg, 0.742 mmol, 51.2% yield) as yellow gummy liquid, LCMS (m/z) 339.1 (M+H)+.

According to the analysis of related databases, 60010-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1201676-03-0 ,Some common heterocyclic compound, 1201676-03-0, molecular formula is C7H4Cl2N2O, 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 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (0.655 g, 3.23 mmol), triethylamine (2.61 g, 25.8 mmol), and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3- a]pyrazine hydrochloride (0.544 g, 3.39 mmol) in dioxane (7.5 ml.) is stirred in a 48 ml_ sealed tube at 12O0C for 16 h. Additional 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine hydrochloride (0.500 g, 3.11 mmol) is added to the mixture, which is heated again at 12O0C for 24 h. A light yellow powder is isolated by filtration of the room temperature reaction mixture (0.61 1 g, 2.10 mmol, 65%). MS(ESI) m/z 291.18 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.1 1 (s, 1 H), 8.50 (s, 1 H), 7.01 (s, 1 H), 4.97 (s, 2 H), 4.68 (s, 2 H), 4.19 (t, J=5.31 Hz, 2 H), 4.01 (t, J=5.43 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1201676-03-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77199-09-8, 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.77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

To a solution of 27 (20.0 g, 86.9 mmol) in DMF (100 mL) wereadded tributyl(vinyl)tin (28.1 mL, 95.6 mmol) and Pd(PPh3)4 (2.01 g, 1.74 mmol), and the mixture was stirred at 100 C for 2 hunder Ar atmosphere. The mixture was diluted with water(200 mL), and extracted with AcOEt (400 mL). The extracts werecombined, washed with brine (200 mL), dried over Na2SO4 andconcentrated in vacuo. The residue was purified by silica gel columnchromatography (hexane/AcOEt = 49/1 to 4/1) to give ethyl5-ethenylpyridine-2-carboxylate (16.5 g, quant.) as pale yellowoil. To a solution of obtained compound above (7.71 g, 43.5 mmol)in EtOH (77 mL) was added 10% Pd-C (1.54 g) and the mixture wasstirred at room temperature for 3 h under H2 atmosphere. The mixturewas filtered through membrane filter, and the filtrate was concentratedin vacuo to give the title compound (7.92 g, quant.) aspale yellow oil. 1H NMR (DMSO-d6) d 1.22 (3H, t, J = 7.6 Hz), 1.33(3H, t, J = 7.1 Hz), 2.71 (2H, q, J = 7.6 Hz), 4.33 (2H, q, J = 7.1 Hz),7.83 (1H, dd, J = 8.0, 2.2 Hz), 7.98 (1H, d, J = 8.0 Hz), 8.58 (1H, d,J = 2.2 Hz).

Statistics shows that 77199-09-8 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-bromopicolinate.

Reference:
Article; Ohashi, Tomohiro; Tanaka, Yuta; Shiokawa, Zenyu; Banno, Hiroshi; Tanaka, Toshio; Shibata, Sachio; Satoh, Yoshihiko; Yamakawa, Hiroko; Yamamoto, Yukiko; Hattori, Harumi; Kondo, Shigeru; Miyamoto, Maki; Tojo, Hideaki; Baba, Atsuo; Sasaki, Satoshi; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4777 – 4791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem