Cesium carbonate → N,N-Dicyclopropyl-6-ethyl-1-methyl-4-(1-methyl-1H-pyrazol-3-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a vial containing 1-methyl-1H-pyrazol-3-amine (11.89 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 mmol), Xantphos (5.90 mg, 10.20 mmol), and cesium carbonate (100 mg, 0.306 mmol) was added 4-bromo-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 97A, 41.0 mg, 0.102 mmol) in DME (1020 μL). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 60° C. for 4 h and 80° C. for 16 h. The reaction mixture was concentrated in vacuo. The crude residue was purified by flash column chromatography using an Isco 40 g column eluting with 0-5% MeOH/CH2Cl2 followed by additional purification with preparative HPLC. N,N-Dicyclopropyl-6-ethyl-1-methyl-4-(1-methyl-1H-pyrazol-3-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (13 mg, 0.030 mmol, 29.5% yield) was isolated as a white solid.

Provenance & Evidence