(5-FLUOROIMIDAZO[1,2-A]PYRIDIN-2-YL)METHANOL synthesis

Yield:878197-92-3 93%

Reaction Conditions:

Stage #1: 5-fluoroimidazo[1,2-a]pyridine-2-carbaldehydewith sodium tetrahydroborate in methanol at 0 - 20; for 2 h;
Stage #2: with water in methanol;

Steps:

13.D

D) (5-FluoroimidazoM .2-alPyridin-2-yl)methanol: A solution of 5-fluoroimidazo[1 ,2-a]pyridine-2-carbaldehyde (80 g, 490 mmol) in methanol (1 L) at O⁰C was treated with sodium borohydride (24 g, 640 mmol) in portions. The reaction was slowly brought to room temperature, stirred for 2 hours, quenched with water, concentrated, dissolved in 3:1 dichloromethane to isopropyl alcohol, and washed with saturated aqueous sodium bicarbonate. The organic layer was separated and the aqueous extracted four times with 3:1 dichloromethane to isopropyl alcohol. The organic layers were combined, dried over sodium sulfate, concentrated, triturated with hexanes, and filtered to yield (5-fluoroimidazo[1,2-a]pyridin-2-yl)methanol (76 g, 93% yield) as a brown solid. ¹H-NMR (CDCI₃): δ 7.59 (s, 1 H), 7.38 (d, 1H), 7.21-7.15 (m, 1 H), 6.43 (m, 1H), 4.85 (S, 2H), 4.45 (s, 1H).

References:

WO2006/76131,2006,A2 Location in patent:Page/Page column 41