Ammonia → (5-aminopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-bromopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Preparation 43, 643 mg, 1.32 mmol) in NMP (1 mL) was added Cu2O (18.9 mg, 0.132 mmol) and 880 ammonia (6 mL) and the reaction heated to 80° C. in a Reactivial™ for 18 hours followed by an additional 18 hours at 90° C. The reaction was cooled and partitioned between water (15 mL) and EtOAc (20 mL). The aqueous layer was extracted twice with EtOAc (2×20 mL), the organic layers combined, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 50:50 DCM:EtOAc to 80:20 EtOAc:MeOH to afford the title compound as a yellow gum (320 mg, 57%).

Provenance & Evidence