Diisopropylethylamine → HCID 178499419, compound

Participants

Reaction Steps

To a stirred solution of impure 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carbaldehyde (49 mg, 0.223 mmol) and trans-3-[(2,3-dichlorophenyl)oxy]cyclobutanamine hydrochloride salt (55 mg, 0.205 mmol) in a mixture of DCM (2 mL) and methanol (2 mL) was added DIPEA (0.039 mL, 0.223 mmol) and sodium triacetoxyborohydride (189 mg, 0.89 mmol). The reaction was stirred at ambient temperature for 3.5 hours when LCMS showed the reaction to be complete. DCM (10 mL) was added and the solution washed with saturated aqueous sodium bicarbonate (10 mL). The organic layer was dried (hydrophobic frit) and concentrated in vacuo. The residue was dissolved in DCM and purified on a silica cartridge (20 g) using a 0-10% methanol-DCM gradient over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow oil (26 mg).

Provenance & Evidence