(2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)METHANOL synthesis

Yield:-

Reaction Conditions:

with methanol;sodium tetrahydroborate at 0 - 20;

Steps:

122

To a solution of sodium borohydride (531 mg, 14.0 mmol) in methanol (30 mL) was added a solution of 2-methylimidazo[l,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[l,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-J₆): δ 2.31 (s, 3H), 4.74 (d, J = 5.4 Hz, 2H), 5.06 (t, J = 5.4 Hz, IH), 6.86 (dt, J = 6.8 Hz, / = 1.3 Hz, IH), 7.16-7.21 (m, IH), 7.42 (td, J = 9.0 Hz, J = 1.2 Hz, IH), 8.28 (td, J = 6.8 Hz, J = 1.2 Hz, IH).

References:

WO2010/132999,2010,A1 Location in patent:Page/Page column 178-179