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ChemicalBook CAS DataBase List 5-Bromo-2-chloro-N-methoxy-N-methylpyridine-3-carboxamide
885223-63-2

5-Bromo-2-chloro-N-methoxy-N-methylpyridine-3-carboxamide synthesis

3synthesis methods
-

Yield:885223-63-2 90%

Reaction Conditions:

Stage #1: 5-bromo-2-chloronicotinic acidwith 1,1'-carbonyldiimidazole in dichloromethane at 20; for 1 h;
Stage #2: N,0-dimethylhydroxylamine in dichloromethane at 20;

Steps:

D-2

Example D-2: Preparation of (2S)-1 -(4-(1 -isopropyl-3-(3-methyl-1 H-pyrazolo[3,4-b]pyridin-5-yl)-1 H- pyrazol-4-yi)pyrimidin-2-ylamino)propan-2-ol D-2-1 D-2-2 D-2-3Preparation of S-bromo^-chloro-N-methoxy-N-methylnicotinamide (D-2-2).D-2-1 D-2-2To a solution of compound D-2-1 (23.5 g, 0.1 mol) in dry CH2CI2 (400 mL) was added CDI (19.5 g, 0.12 mol) portionwise at room temperature under N2 atmosphere. After the addition, the mixture was stirred for 1 hour. O,N-dimethyl-hydroxylamine (11.5 g, 0.12 mol) was then added portionwise at room temperature. After the addition, the resulting mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 8:1 ) indicated complete consumption of starting material. H2O (200 mL) was added and the organic layer was separated, washed with 1 N HCI (100 mL), 1 N Na2CO3 (100 mL) and saturated aqueous NaCI (200 ml_) in sequence, dried over Na2SO4 and concentrated in vacuo to give compound D- 2-2 (25 g, 90%) as a yellow solid.

References:

WO2009/16460,2009,A2 Location in patent:Page/Page column 102-104

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