Day: April 18, 2022

Electric Literature of 57963-08-3, Adding some certain compound to certain chemical reactions, such as: 57963-08-3, name is 5,6-Dimethylpyridin-2-amine,molecular formula is C7H10N2, 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 57963-08-3.

Step 1 Ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate A heavy walled sealable tube was charged with ethyl 4,6-dichloropyridazine-3-carboxylate (300 mg, 1.36 mmol) and 5,6-dimethylpyridin-2-amine (249 mg, 2.04 mmol). To the mixture was added acetonitrile (8.00 mL) and the reaction mixture was heated with stirring in an oil bath at 140 C. for 20 h. After cooling to room temperature the residue was suspended in dichloromethane and purified by flash chromatography (silica 20-45 muM, 40 g, Thomson) eluting with 0 to 10% over 20 min, acetone/dichloromethane to give ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate (195 mg, 46.8%) as an off-white solid. 1H NMR (CHLOROFORM-d) delta: 10.54 (s, 1H), 9.14 (s, 1H), 7.41 (d, J=8.3 Hz, 1H), 6.70 (d, J=8.3 Hz, 1H), 4.55 (q, J=7.2 Hz, 2H), 2.50 (s, 3H), 2.26 (s, 3H), 1.50 (t, J=7.2 Hz, 3H); LC-MS 307.0 [M+H]+.

According to the analysis of related databases, 57963-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 628691-93-0, 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 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Diphenylphosphoryl azide (DPPA) (129 mmol) wasadded to a mixture of 2-chloro-3-fluoro-pyridine-4-carbox- ylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-l3uOH/ toluene (200 mE). The mixture was heated at 110 C. for 4 h. Mixture was diluted with H20 and extracted with DCM. The organic layer was dried (Na2504) and concentrated. The residue was purified by flash column chromatography (5i02, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate.

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 628691-93-0, 2-Chloro-3-fluoroisonicotinic acid.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
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. 77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C13H11NO3

Step 3; 6-Oxo-l -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-l -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; *H NMR (400 MHz, DMSO-d6) delta 6.53 (d, / = 9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, / = 2.5, 9.8 Hz , 1H), 8.23 (d, / = 2.5 Hz, 1H); IR (KBr) upsilon 3446, 1708, 1645, 1577, 1263, 1228 cm”1; MS 214 (M – 1).

The synthetic route of 77837-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; SOMMERS, Andreas; WO2012/122165; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1228631-54-6, 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. 1228631-54-6, name is 1-(6-(Trifluoromethyl)pyridin-3-yl)ethanol, molecular formula is C8H8F3NO, 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.

Example 69: Preparation of Carbamates – General Method AThe acyl azide was suspended in dry toluene (0.35 M). To the resulting slurry was added the appropriate alcohol (1.20 equiv). The slurry was heated to 100 0C (external) for 4-24 h and then cooled to ambient temperature. The product was isolated by vacuum filtration or purified by silica gel column chromatography (after applying the material directly to the column) eluting with EtOAc/hexanes gradient. In some instances, further purification by recrystallization was necessary. Typical solvents used include: chloroform-Patent; DOW AGROSCIENCES LLC; LAMBERT, William; CROUSE, Gary; SPARKS, Thomas; CUDWORTH, Denise; WO2011/17513; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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.915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, molecular formula is C5H4BrIN2, molecular weight is 298.91, as common compound, the synthetic route is as follows.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%). To a mixture containing 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) and Intermediate 5A-2 (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (111 mg, 0.36 mmol), and Pd(dppf)C12 (10.5 mg, 0.014 mmol) in a screw cap vial was added THF (2.5 mL) followed by 3M aqueous solution of tripotassium phosphate (0.10 mL, 0.3 mmol). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 75 C. for 3 h. The reaction mixture was cooled to room temperature and treated with saturated aqueous NaCl solution (5 mL) and extracted with ethyl acetate (3*10 mL). The extracts were combined, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified on silica gel column chromatography eluting with a 10 min gradient from 5%-100% DCM/EtOAc. No separation was observed. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate was isolated (100 mg, 77% yield), m/z (550, M+1) and was used as such in subsequent step. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (95 mg, 0.21 mmol) was dissolved in MeOH (5 mL) and transferred to a Parr bottle. The mixture was purged with nitrogen. Pearlman’s Catalyst (25 mg, 0.036 mmol) was added and the bottle was pressurized with hydrogen gas (50 psi) and shaken for 22 h. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated. The resulting residue was dissolved in a small amount of DCM and charged to a silica gel column, which was eluted over a 10 min gradient with 1%-5% MeOH/DCM to afford a mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5C) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (82 mg, 80%), m/z (452, M+H). The mixture of isomers (tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)piperidine-1-carboxylate (Intermediate 5C) and tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)piperidine-1-carboxylate (80 mg, 0.18 mmol) were suspended in 4 N HCl in dioxane (4 mL, 16.00 mmol), stirred for 30 min, and concentrated to dryness. The resulting residue was suspended in diethyl ether (1 mL) and the solids were filtered and dried to give a mixture of 2-(3,4-dimethoxyphenyl)-3-methyl-5-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine (Intermediate 5D) and 3-(3,4-dimethoxyphenyl)-2-methyl-5-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine as bis HCl salts (50 mg, 65%), m/z (352, M+H). To a solution containing a mixture of 3-(3,4-dimethoxyphenyl)-2-methyl-5-(piperidin-4-yl)-1H-pyrrolo[2,3-c]pyridine 2 HCl (Intermediate 5D) and 2-(3,4-dimethoxyphenyl)-3-methyl-5-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine, 2 HCl (30 mg, 0.07 mmol) in DMF (1 mL) was added 1-isobu…

Statistics shows that 915006-52-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-2-iodopyridin-3-amine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 863704-60-3, 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.863704-60-3, name is 6-(4-Fluorophenyl)picolinic acid, molecular formula is C12H8FNO2, molecular weight is 217.2, as common compound, the synthetic route is as follows.

A mixture of Intermediate 3-07 (156 mg, 0.72 mmol), HATU (394 mg, 1.0 mmol) and DIPEA (0.639 mL, 3.66 mmol) in DCM (6 mL) was stirred at RT for 15 min. A solution of Intermediate 3-04 (155 mg, 0.72 mmol) in DCM (4 mL) was added and the reaction mixture was stirred at RT for 14 h. The mixture was washed with water, and the organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (Biotage, cHex:EtOAc, 85:15 to 50:50) to afford Intermediate 3-09 (298 mg, 100%).

Statistics shows that 863704-60-3 is playing an increasingly important role. we look forward to future research findings about 6-(4-Fluorophenyl)picolinic acid.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; ALVAREZ ESCOBAR, Rosa Maria; GARCIA GARCIA, Ana Belen; RIESCO FAGUNDO, Rosario Concepcion; BLANCO APARICIO, Carmen; WO2012/98387; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1003-56-1 ,Some common heterocyclic compound, 1003-56-1, 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.

Preparation 5: 1-(4-chlorobutyl)-3-methyl-2(1H)-pyridinone (Prep5); To a solution of 3-methyl-2(1 H)-pyhdinone (commercial aldrich) (200 mg, 1.85 mmol), in dry DMF (5 mL), K2CO3 (0.51 g) and 1-bromo-3-chlorobutane (0.32 mL) were added and the resulting mixture was heated at 90 C for 5 hours After solvent elimination under reduced pressure, the residue was diluted with ethyl acetate and washed once with water and once with brine The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure The crude product was purified by silica gel chromatography eluting with cyclohexane/EtOAc 8 2 to give the title compound as colourless oil (0 24 g) MS (m/z): 200 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-56-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/113258; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113209-90-8, 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. 113209-90-8, name is (4-Chloro-5-fluoropyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

(v) Substituting 2-hydroxymethyl-4-chloro-5-fluoropyridine (2.5 g) for 2-hydroxymethyl-3-fluoro-4-chloropyridine and using corresponding molar proportions of the other reagents in the method of Example 27(v), gave 2-hydroxymethyl-4-morpholino-5-fluoropyridine (2.08 g) m.p. 134-136 (from acetonitrile).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113209-90-8, (4-Chloro-5-fluoropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline & French Laboratories Limited; US5250527; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22918-01-0, 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. 22918-01-0, name is 2-Bromo-4-chloropyridine. A new synthetic method of this compound is introduced below.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70C was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C for another 1 h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL * 3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO) delta 10.21 (s, 1H), 8.52 (d, J= 5.5 Hz, 1H), 7.79 (d, J= 5.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22918-01-0, 2-Bromo-4-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 623942-84-7, 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.623942-84-7, name is (3-Bromo-6-methoxypyridin-2-yl)methanol, molecular formula is C7H8BrNO2, molecular weight is 218.05, as common compound, the synthetic route is as follows.

(3-bromo-6-methoxypyridin-2-yl)methanol (2.5 g, 11.4 mmol) and CBr4 (4.5 g, 13.6 mmol) were added into DCM (30 mL). PPh3 (3.6 g, 13.6 mmol) in DCM (10 mL) was added dropwise into the reaction mixture at 0 C. The mixture was stirred at 0 C for 0.5 hour. The reaction was concentrated to give a residue. The residue was purified by flash silica gel chromatography (40 g column, EtOAc in petroleum ether from 0% to 10%) to afford 3- bromo-2-(bromomethyl)-6-methoxypyridine (2.69 g, 84% yield) as a colorless oil. LCMS m/z [M+H]+ = 281.8.

Statistics shows that 623942-84-7 is playing an increasingly important role. we look forward to future research findings about (3-Bromo-6-methoxypyridin-2-yl)methanol.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem