Dimethylformamide → HCID 69620982, compound

Participants

Reaction Conditions

Reaction Steps

To DMF (11 ml, 225 μmol) in a sealed tube flushed with nitrogen was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (47 mg, 0.225 mmol), (S)-tert-butyl 1-(6-bromoindolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (100 mg, 225 μmol), sodium carbonate solution (629 μl, 629 mmol), 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. LCMS indicated a trace of starting material remained. Another aliquot of Pd(dppf)Cl2 (9.2 mg, 11 μmol) was added and the slurry stirred for an additional 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-(6-(1-methyl-1H-pyrazol-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (67 mg, 67%). MS ESI (pos.) m/e: 447.3 (M+H).

Provenance & Evidence