Cesium carbonate → 3-Methyl-4-{[1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]amino}benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine (100 mg), 4-amino-3-methylbenzonitrile (57 mg), cesium carbonate (163 mg), tris(dibenzylideneacetone)dipalladium (0) (7 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (5 mg) in 1,4-dioxan (2 ml) was heated to 100° C. under argon overnight. The reaction mixture was diluted with dichloromethane and washed with water, followed by saturated sodium chloride solution, then dried (MgSO4), filtered and evaporated. The residue was triturated with 2:1:1 methanol/dimethylsulfoxide/diethyl ether to yield an off white solid. This was dissolved in 1:1 methanol/dichloromethane and a solution of 1.0M hydrochloric acid in diethyl ether (1.4 ml) and the solvent evaporated to afford the title compound as an off white solid (36 mg).

Provenance & Evidence