Sodium Carbonate → HCID 69620984, compound

Participants

Reaction Conditions

Reaction Steps

To DMF (1.1 ml) in a sealed tube flushed with nitrogen was added 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (62 mg, 230 μmol), (S)-tert-butyl 1-(6-bromoindolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (100 mg, 230 μmol), 1M sodium carbonate solution (630 μl, 630 μmol), and 1,1′-dis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (Pd(dppf)Cl2) (9.2 mg, 11 μmol). The slurry was heated to 85° C. and stirred for three hours. A significant amount of starting material remained. Another portion of (Pd(dppf)Cl2) (9.2 mg, 11 μmol) was added and the reaction was stirred for eight hours. The reaction was then allowed to cool to room temperature. The reaction was diluted with water and extracted with ethyl acetate (2×40 mL). The combined organic layers were washed with 1M lithium chloride solution (1×30 mL) and brine (1×30 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica, 0 to 60% ethyl acetate:hexanes) to give tert-butyl (S)-1-oxo-3-phenyl-1-(6-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)indolin-1-yl)propan-2-ylcarbamate (34 mg, 29% yield). MS ESI (pos.) m/e: 433.1 (M+H-THP).

Provenance & Evidence