Imidazole → 2-(Methylthio)-6-{[(triisopropylsilyl)oxy]methyl}nicotinonitrile

Participants

Reaction Steps

To a solution of 6-formyl-2-(methylthio)nicotinonitrile (1.0 g, 5.6 mmol) in methanol (10 ml) was slowly added sodium borohydride at 0° C. with stirring, and the resulting mixture was stirred at the same temperature for 10 minutes. After evaporating the solvent in vacuo, the residue obtained was diluted with ethyl acetate, poured into water (20 ml) and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue obtained and imidazole (0.76 g, 11 mmol) in N,N-dimethylformamide (6 ml) was added triisopropylsilyl chloride (1.3 ml, 6.2 mmol) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, the reaction mixture was poured into water (20 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 3:97) as the eluent to afford the title compound (1.7 g) in a yield of 91% as a colourless oily product.

Provenance & Evidence