Sodium hydride → 2-(2-Aminopyridin-4-ylmethylthio)-N-(tert-butoxycarbonylmethyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Participants

Reaction Steps

A solution of 2-(2-aminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (the free base of Compound No. 3-1, 50 mg, 0.14 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added dropwise to a suspension of 60% sodium hydride (13 mg, 0.30 mmol) in anhydrous N,N-dimethylformamide (1.0 mL) under ice-cooling, and the mixture was stirred for 5 minutes. Bromoacetic acid tert-butyl ester (22 μL, 0.15 mmol) was added to the reaction mixture, and the mixture was stirred for 30 minutes at room temperature. The mixture was poured into ice water (15 mL), and the whole was extracted with ethyl acetate (15 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 45 mg of the target compound as a colorless amorphous. (Yield 69%)

Provenance & Evidence