Water → methyl 3-((7-cyano-1-cyclopentyl-4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)amino)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-1-cyclopentyl-4-methoxy-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile (1.5 g) obtained in Step H of Example 33, methyl 3-aminobenzoate (0.85 g), 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (0.54 g) and tris(dibenzylideneacetone)dipalladium(0) (0.43 g) in toluene (10 mL) was added sodium tert-butoxide (0.90 g), and the mixture was stirred at 110° C. for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (190 mg).

Provenance & Evidence