Diiodomethane → 4-iodo-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (34.4 mg, 0.102 mmol) in diiodomethane (102 μL) at 60° C. was slowly added isoamyl nitrite (27.4 μL, 0.203 mmol). The reaction mixture was stirred at 60° C. 5 h. After cooling to rt, the reaction mixture was diluted with dichloromethane. Saturated aqueous sodium bicarbonate was added and the aqueous layer was extracted with dichloromethane (3×). The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was placed on the pump for 16 h to remove any additional diiodomethane. LCMS was deemed pure enough to be carried forward crude. The product was used immediately in the next reaction.

Provenance & Evidence