2-methylimidazo[1,2-a]pyridine-3-carbaldehyde → (2-methylimidazo[1,2-a]pyridin-3-yl)methanol

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Reaction Steps

To a solution of sodium borohydride (531 mg, 14.0 mmol) in methanol (30 mL) was added a solution of 2-methylimidazo[1,2-a]pyridine-3-carbaldehyde (1.5 g, 9.4 mmol) in methanol (5 mL) at 0° C. The mixture was stirred for 2 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, {2-methylimidazo[1,2-a]pyridin-3-yl}methanol was obtained (914 mg, 59% yield) and used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 2.31 (s, 3H), 4.74 (d, J=5.4 Hz, 2H), 5.06 (t, J=5.4 Hz, 1H), 6.86 (dt, J=6.8 Hz, J=1.3 Hz, 1H), 7.16-7.21 (m, 1H), 7.42 (td, J=9.0 Hz, J=1.2 Hz, 1H), 8.28 (td, J=6.8 Hz, J=1.2 Hz, 1H).

Provenance & Evidence