Dichloromethane → Ethyl 3-({[(1,1-dimethylethyl)(diethyl)silyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-8-carboxylate (2.7 g, 12.26 mmol) in DCM (100 mL) under nitrogen was added tert-butylchlorodimethyl silane (4 g, 26.5 mmol), 4-dimethylamino pyridine (0.32 g, 2.62 mmol) and triethylamine (3 mL, 21.52 mmol) and the reaction mixture heated at 50° C. under nitrogen for 16 hours. The mixture was concentrated in vacuo and the residue was dissolved in DCM and purified on a silica cartridge (100 g) using a 0-30% methanol-DCM gradient over 60 mins. The product containing fractions were combined and evaporated in vacuo to give the title compound as an off-white solid (4.174 g).

Provenance & Evidence