(4-Methoxyphenyl)boronic acid → (S)-tert-Butyl 4-(1-cyano-2-(4'-methoxybiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 4-(1-cyano-2-(4-iodophenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 15, step (i), 317 mg) in acetonitrile (5 mL) under nitrogen was treated with 4-methoxyphenylboronic acid (96 mg) followed by an aqueous solution of potassium acetate (2M, 0.65 mL) and 1,1 bis(bi-tert-butylphosphino)ferrocene palladium dichloride (8 mg). The reaction mixture was stirred at 75° C. for 18 h and then evaporated, dissolved in dichloromethane and absorbed onto silica. Purification by chromatography on silica eluting with 50% ethyl acetate in isohexane and then 100% ethyl acetate afforded the sub-titled compound as a solid (120 mg).

Provenance & Evidence