IMidazo[1,2-a]pyridine-3-Methanol, 6-broMo- synthesis

Yield:30489-47-5 73%

Reaction Conditions:

with methanol;sodium tetrahydroborate;water in dichloromethane at 20; for 2 h;

Steps:

1 Step 1: Preparation of (6-bromoimidazo[1,2-a]pyridin-3-yl) methanol

To solid NaBH₄ (8 mg, 0.227 mmol) was added water (0.1 mL) and then 6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde (100 mg, 0.444 mmol), MeOH (0.7 mL) and DCM (0.7 mL) were added and the reaction mixture was stirred at rt for 2 h. The mixture was concentrated under reduced pressure and the material was triturated with ether and then concentrated under reduced pressure to provide the title compound (74 mg, 73%). ¹H NMR (500 MHz, DMSO) δ 8.65 (d, J=1.1 Hz, 1H), 7.57 (d, J=9.1 Hz, 1H), 7.53 (s, 1H), 7.38 (dd, J=9.5, 1.9 Hz, 1H), 5.29 (bs, 1H), 4.80 (s, 2H); MS (ESI) [M+H]⁺ 227.0/229.0;

References:

WO2017/66876,2017,A1 Location in patent:Page/Page column 61; 62; 63