Water → HCID 68809622, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 7-oxo-8-(2-propen-1-yl)-7,8-dihydro-1,8-naphthyridin-2-yl trifluoromethanesulfonate (697 mg, 2.087 mmol) in DMF (10 ml) was added Zn(CN)2, (147 mg, 1.252 mmol) Pd2(dba)3 (48 mg, 0.052 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (58 mg, 0.104 mmol). The reaction was then heated at 50° C. for 1 h and then at 70° C. for a further 1 h and at 100° C. for a further 1 h. More Zn(CN)2, (147 mg, 1.252 mmol) Pd2(dba)3 (48 mg, 0.052 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (58 mg, 0.104 mmol) was then added and the reaction was heated at 100° C. for a further 1 h. The reaction was then cooled and treated with water (200 ml). The reaction was then extracted with DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using an ethyl acetate/hexane gradient to provide the desired compound (374 mg, 85%).

Provenance & Evidence