Sodium Carbonate → (S)-tert-Butyl 4-(1-amino-3-(4-(3-(2-methoxyethyl)-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), 250 mg) in acetonitrile (8 mL) with 5-bromo-3-(2-methoxyethyl)benzo[d]oxazol-2(3H)-one (Example 24, step (i), 131 mg) was treated with an aqueous solution of sodium carbonate (2M, 0.483 mL). Nitrogen was bubbled through the solution and then 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added. The reaction mixture was heated at 85° C. for 18 h under nitrogen and allowed to cool to room temperature. Purification by chromatography on silica eluting with 50-100% ethyl acetate/isohexane as eluent afford the sub-titled compound (66 mg).

Provenance & Evidence