Sodium Carbonate → 1,1-Dimethylethyl 3-(5-cyano-1-isoquinolinyl)propanoate

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 3-(5-bromo-1-isoquinolinyl)propanoate (D34; 60 g, 178 mmol) was taken up in dry DMA (600 ml) followed by the addition of potassium hexacyanoferrate hexahydrate (22.61 g, 53.5 mmol) then palladium acetate (0.801 g, 3.57 mmol) dppf (3.96 g, 7.14 mmol) and then finally sodium carbonate (22.7 g, 214 mmol). The reaction mixture was stirred at 120° C. overnight, cooled and diluted with ethyl acetate (500 ml) and filtered through Celite. The filtrate was concentrated in vacuo. and the dark residue was taken up in DCM (250 ml) and filtered through Celite and cotton wool. The DCM solution (250 ml) was purified by chromatography using a gradient system 0-100% ethyl acetate in isohexane to give the title compound (25.3 g)

Provenance & Evidence