Potassium Carbonate → (S)-tert-Butyl 4-(1-amino-3-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 4-(1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 224 mg) in acetonitrile (10 mL) under nitrogen was treated with 5-bromo-3-methylbenzo[d]oxazol-2(3H)-one (99 mg) followed by an aqueous solution of potassium carbonate (2M, 0.433 mL) and 1,1 bis(bi-tert-butylphosphino)ferrocene palladium dichloride (6 mg). The reaction mixture was stirred at 75° C. for 18 h and then evaporated to an oil, 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 (150 mg).

Provenance & Evidence