Month: April 2022

Related Products of 153747-97-8 ,Some common heterocyclic compound, 153747-97-8, molecular formula is C14H20BrN3O2, 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.

The gaseous trifluororacetaldehyde was trapped with the dry ice-filled cold finger and dripped into a THF solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (1 g, 2.92 mmol) with 2.5 M n-butyllithium in hexanes (1.29 mL, 3.2 mmol) at -78 C under nitrogen atmosphere. After addition, the reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was quenched with saturated ammonium chloride aqueous solution at -78 0C and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford a light yellow solid. The crude material was purified by flash chromatography on silica gel, eluting with 10 – 80% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford a colorless sticky solid (450 mg, 35.9% yield). The Boc protected titled compound (200 mg, 0.466 mmol) was stirred in 50% TFA in DCM (5 mL) for 10 min. The reaction mixture was concentrated to afford the titled product as a TFA salt (150 mg, yield 98%). MS (m/z, MH+): meas. 330.0 calc. 329.25

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. 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63237-88-7, Adding some certain compound to certain chemical reactions, such as: 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid,molecular formula is C8H6N2O2, 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 63237-88-7.

Step 2B: Synthesis of N-{4-[(pyrimidin-2-yl)({[2-(trimethylsilyl)ethoxy]methyl}) sulfamoyl] phenyl}pyrazolo[l,5-a]pyridine-2-carboxamide 13.1 [00307] Methanesulfonyl chloride (0.04ml, 0.55mmol) was added to a stirred mixture of 4- amino-N-(pyrimidin-2-yl)-N- { [2-(trimethylsilyl)ethoxy]methyl} benzene- 1 -sulfonamide (9.1, 150mg, 0.39mmol), pyrazolo[l,5-a]pyridine-2-carboxylic acid (60mg, 0.39mmol) and 3-picoline (0.12 ml, 1.18mmol) in MeCN (dry, 5ml) at 0C. After addition the reaction mixture was allowed to reach rt and stirred for 15h. The reaction mixture was partitioned between DCM (50ml) and water (50ml). The aqueous layer was further extracted with DCM (2x 30ml) and the combined layers dried over Na2S04. The solvent was removed in vacuo to afford a material which was purified by flash column chromatography (heptane/EtOAc 75/25 to 0/100) to obtain 190mg (87%) of N-{4-[(pyrimidin-2-yl)({[2-(trimethylsilyl)ethoxy]methyl}) sulfamoyl]phenyl}pyrazolo[l,5-a]pyridine-2-carboxamide 13.1 as an off white solid.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59020-10-9, 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 59020-10-9, name is 3-(Tributylstannyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Pd(PPh3)2Cl2 (3.84 mg, 0.0054mmol) was added to a solution of ((S)- 1-(N1^- Bromo-benzyl)-N’-[(S)-3-hydroxy-3-((lS,2R)-2-hydroxy-indan-l-ylcarbamoyl)-4- phenyl-butyl]-hydrazinocarbonyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester (22) (75 mg, 0.108 mmol), 3-(l,l,l-tri-?-butylstannyl)pyridine (159 mg, 0.431 mmol) and CuO (8.6 mg, 0.108 mmol) in DMF (2.0 mL) and stirred in a heavy-walled Smith process EPO vial at 120 0C 50 min in the microwave cavity. The mixture was diluted with CH2Cl2 (20.0 mL) and washed with aq. saturated NaHCO3 (3 x 15.0 mL). The organic layer was dried (MgSO4) and evaporated. The residue was re-dissolved in CH3CN (50.0 mL) and washed with isohexane (3 x 20.0 mL). The acetonitrile phase was evaporated and the crude product was purified using RP-LC-MS (45 min gradient of 15-70% CH3CN in 0.05% aqueous formic acid) which gave the title product (23.1 mg, 31%) as a white solid. MS (ESI+): m/z: 694 (M+);1H NMR (CD3OD 400 MHz): delta 8.66 (m, IH), 8.45 (m, IH), 8.00 (m, IH), 7.52-7.44 (m, 6H), 7.30-7.04 (m, 9H), 5.04 (m, IH), 4.24 (m, IH), 3.82 (m, 2H), 3.68 (s, IH)5 3.60 (s, 3H), 3.10-2.78 (m, 6H), 2.62 (s, IH), 2.20 (m, IH), 1.96 (m, IH), 0.78 (s, 9H); 13C NMR (CD3OD, 100 MHz): delta 176.9, 171.1, 157.8, 147.8, 147.0, 141.3, 140.3, 137.0, 136.8, 135.2, 130.5, 130.0, 127.6, 126.8, 126.5, 126.3, 124.9, 124.1, 78.7, 72.5, 61.9, 61.7, 57.2, 53.6, 51.5, 39.6, 34.3, 33.5, 28.3, 25.7

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 59020-10-9, 3-(Tributylstannyl)pyridine.

Reference:
Patent; MEDIVIR AB; WO2006/84688; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 135124-71-9, 5-(Hydroxymethyl)nicotinonitrile, 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, 135124-71-9, blongs to pyridine-derivatives compound. Product Details of 135124-71-9

d) 5-Cyano-pyridine-3-carbaldehyde A black suspension of (5-cyano-pyridin-3-yl)-methanol (0.070 g, 0.52 mmol), anhydrous CH2Cl2 (1.04 mL) and manganese oxide (0.181 g, 2.09 mmol) was heated to reflux and monitored by TLC. After 8 h, the reaction mixture was cooled to room temperature and additional manganese oxide (0.095 g, 1.1 mmol) was added to the reaction flask. The reaction mixture was then heated to reflux. After 18 h, the reaction was still not complete by TLC and additional manganese oxide (0.097 g, 1.1 mmol) was added to the reaction flask. After heating at 60 C. for 72 h, the reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL), passed through celite and washed with additional EtOAc (50 mL). The organic filtrate was dried over MgSO4, filtered through sintered glass and concentrated to yield 0.064 g (93%) of a white solid. It was purified by column chromatography (elution with EtOAC:hexanes, 1:3) and yielded 0.038 g (55%) of the title compound as a white solid. 1H NMR (CDCl3): 10.17 (s, 1H), 9.28 (d, J=1.9 Hz, 1H), 9.11 (d, J=2.2 Hz, 1H), 8.45 (dd, J=2.2, 1.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135124-71-9, its application will become more common.

Reference:
Patent; Cytovia, Inc.; US2006/104998; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 483324-01-2 , The common heterocyclic compound, 483324-01-2, name is 2-Chloro-4-(pyridin-3-yl)pyrimidine, molecular formula is C9H6ClN3, 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 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure

The synthetic route of 483324-01-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anli, Huang; Xing, Liu; Zelikovitch, Lior; Kaspi, Joseph; US2006/149061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1039055-46-3, tert-Butyl (5-aminopyridin-2-yl)(methyl)carbamate, 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, COA of Formula: C11H17N3O2, blongs to pyridine-derivatives compound. COA of Formula: C11H17N3O2

To 0.356 g (1.53 mmol) of the above amine in THF (3 mL) was added 0.70 mL of n-butyllithium (2.5 M solution in hexanes) and the mixture was stirred for 10 min. A solution of 0.21 g (0.52 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added, and the resulting mixture was stirred for 1 hr. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH3, and dried. The solvent was removed under vacuum, and the product mixture was purified by flash column chromatography, eluting with CH2Cl2/EtOAc (3:1), to give 0.075 g (13% yield) of tert-butyl 5-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]amino}-2-pyridinyl(methyl)carbamate, as a yellow powder: 1H NMR (DMSO-d6) delta 10.11 (s, 1H), 8.68-7.41 (m, 5H), 7.61 (d, J=9.0 Hz, 1H), 6.97 (d, J=8.1 Hz, 1H), 3.98 (s, 3H), 3.83 (s, 4H), 3.74-3.73 (m, 4H), 3.29 (s, 3H), 1.47 (s, 9H); LCMS (APCI+) m/z: 585 (MH+, 100%).

The synthetic route of 1039055-46-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pathway Therapeutics Limited; US2010/249099; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 777931-67-6, 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. 777931-67-6, name is 3-Bromo-2-chloro-6-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.

To a round bottom flask was added 3-bromo-2-chloro-6-methoxypyridine (10.57 g), cyclopropyl boronic acid (4.28 g), palladium acetate (533 mg), (0887) tricyclohexylphosphine (1.33 g) and potassium phosphate (35.2 g). To this solid mixture was added toluene:H2O (158 mL; 9:1 ratio). The heterogeneous mixture was purged with a nitrogen stream for 1 min and then was heated at reflux overnight. The reaction mixture was diluted with EtOAc (100 mL) and water (100 mL). The phases were separated and the aqueous phase was backextracted twice with ethyl acetate (100 mL each). The combined organic phases were dried over magnesium sulfate and the crude residue was purified by flash chromatography (ethyl acetate / hexanes as the eluents) yielding 8.6 grams of 2-chloro-3-cyclopropyl-6-methoxypyridine as a colorless oil. LCMS method A: Rt = 0.61 min; (M+H)+ = 222.2, 224.2.1H NMR (CD3OD): delta 8.45 (s, 1H), 8.33 (s, 1H), 3.90-4.00 (m, 2H), 3.70-3.80 (m, 2H), 3.20-3.55 (m, 4H), 1.80-2.0 (m, 4H), 1.27 (s, 9H).

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 777931-67-6, 3-Bromo-2-chloro-6-methoxypyridine.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (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.83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine, molecular formula is C12H10BrNO, molecular weight is 264.12, as common compound, the synthetic route is as follows.SDS of cas: 83664-33-9

6-Benzyloxy-pyridine-3-carbaldehyde To a solution of 2-benzyloxy-5-bromo-pyridine (1.64 g, 6.2 mmol) in tetrahydrofuran (25 mL, -78 C.) was added n-butyllithium (2.5 M in hexane, 2.61 mL, 1.05 equiv). After 1 h at -78 C., dimethylformamide (0.97 mL, 2 equiv) was added and the mixture stirred for 30 min. The reaction was quickly poured into a stirred solution of 5% aqueous sodium bicarbonate (50 mL) and extracted with diethyl ether (3*). The ethereal was washed with brine, dried over magnesium sulfate, and concentrated to give 1.16 g (quant.) which was used without purification. Mass spec.: 186.34 (MH)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83664-33-9, 2-(Benzyloxy)-5-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Chaturvedula, Prasad V.; Chen, Ling; Civiello, Rita; Conway, Charles Mark; Degnan, Andrew P.; Dubowchik, Gene M.; Han, Xiaojun; J. Jiang, Xiang Jun; Karageorge, George N.; Luo, Guanglin; Macor, John E.; Poindexter, Graham; Tora, George; Vig, Shikha; US2004/204397; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4966-90-9, 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-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, 4966-90-9, blongs to pyridine-derivatives compound. Safety of 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one

Part A: 2,4-Dihydroxy-6-methyl-3-nitropyridine was added to phosphorous oxychloride in a manner similar to Part B of Example 1 to afford 2,4-dichloro-3-nitro-6-methylpyridine as a pale yellow solid (mp 69-70 C.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4966-90-9, its application will become more common.

Reference:
Patent; Dupont Pharmaceuticals; US6107300; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52378-63-9, 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. 52378-63-9, name is (3-Aminopyridin-2-yl)methanol, molecular formula is C6H8N2O, 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.

(i) A solution sodium nitrite (2.38 g.) in water (10 ml.) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g.) in aqueous hydrobromic acid (48%, 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous bromide (2.5 g.) in 60% hydrobromic acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-bromo-2-hydroxymethyl-pyridine (4.8 g.).

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 52378-63-9, (3-Aminopyridin-2-yl)methanol.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4025527; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem