N,N'-Dimethylethylenediamine → HCID 52935645, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid (6-bromopyridin-3-ylmethyl)-amide (133 mg, 0.313 mmol) in DMSO (2 mL) in a microwave tube is added sodium methanesulfinate (52.0 mg, 0.509 mmol), copper (II) trifluoromethanesulfonate (115 mg, 0.318 mmol) and N,N′-dimethylethylene diamine (0.100 mL, 0.939 mmol). The mixture is warmed at 110° C. for 35 minutes in a microwave reactor. The reaction is the diluted with saturated aqueous ammonium chloride (7 mL) and extracted with EtOAc (4×7 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (3×7 mL) and brine (3×7 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0.5-3% methanol in dichloromethane. The resulting solid is triturated with dichloromethane-ether to afford the title compound.

Provenance & Evidence