Sodium Carbonate → (S)-tert-Butyl 4-(1-amino-3-(3'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 350 mg) in acetonitrile (7 mL) under nitrogen was treated with 3-cyanophenylboronic acid (99 mg) followed by aqueous sodium carbonate (2M, 0.677 mL). Nitrogen was bubbled through and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (10 mg) was added. The mixture was stirred at 85° C. for 25 h. The solvent was partially evaporated and the solution was purified by chromatography on silica using 50% ethyl acetate in isohexane and then ethyl acetate as eluent to afford the sub-titled compound as a solid (316 mg).

Provenance & Evidence