Dimethylformamide → 1-(3-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propyl)-5-isoquinolinecarbonitrile

Participants

Reaction Steps

A microwave vial was charged with 5-bromo-1-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)isoquinoline (D11; 640 mg, 1.68 mmol), dry, degassed N,N-dimethylformamide (DMF) (8 ml), zinc cyanide (217 mg, 1.85 mmol) and tetrakis(triphenylphosphine)palladium(0) (194 mg, 0.168 mmol). The reaction vessel was sealed and heated using microwave irradiation to 120° C. for 60 min. After cooling, the mixture was diluted with ethyl acetate, the organic layers partitioned with water (×3) and the aqueous layer discarded. The organic layers were passed through a hydrophobic frit before being concentrated in vacuo. The resultant yellow oil was purified by flash column chromatography on silica using 2% to 20% ethyl acetate in cyclohexane as eluent. The relevant fractions were pooled and concentrated in vacuo to give the title compound as a yellow oil (417 mg).

Provenance & Evidence