6-(Hydroxymethyl)imidazo[1,2-a]pyridine

Definition

Synthesis

139022-25-6

132213-07-1

To a solution of imidazo[1,2-a]pyridine-6-carboxylic acid (4.3 g, 27 mmol) in anhydrous tetrahydrofuran (25 mL) was added slowly and dropwise borane dimethyl sulfide complex (5.8 mL, 10 N, in dimethyl sulfide, 58 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 0.5 h, then warmed up to 80 °C and kept stirring for 3 h. The reaction mixture was then stirred for 0.5 h. The reaction mixture was cooled down to 0.5 °C. Upon completion of the reaction, the mixture was cooled to 0 °C, carefully quenched with methanol (10 mL) and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with an eluent ratio of dichloromethane: methanol = 10:1 to afford imidazo[1,2-a]pyridine-6-methanol (1.0 g, 26% yield) as a white solid.LCMS analysis resulted in (ES+) m/z (M+H)+ = 149.1 and retention time tR = 0.279 min.

References