Sodium Carbonate → HCID 67497592, compound

Participants

Reaction Conditions

Reaction Steps

Pyrimidin-5-ylboronic acid (28 mg, 230 μmol), (S)-tert-butyl 1-(6-bromoindolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (100 mg, 230 μmol), (Pd(dppf)Cl2) (18 mg, 22 μmol) were dissolved in DMF (1.1 mL) and 1M sodium carbonate solution (630 μl, 630 μmol) was added. The resulting slurry was stirred in a sealed tube for one hour at 85° C., allowed to cool to room temperature and diluted with water. The mixture was extracted with ethyl acetate (2×50 mL). The organic layers were combined and washed with 1M lithium chloride solution (1×25 mL) and brine (1×25 mL) and dried over magnesium sulfate. The residue was purified by medium pressure chromatography (silica, 0 to 100% ethyl acetate:hexanes) to give (S)-tert-butyl 1-oxo-3-phenyl-1-(6-(pyrimidin-5-yl)indolin-1-yl)propan-2-ylcarbamate (74 mg, 74% yield). MS ESI (pos.) m/e: 445.1 (M+H).

Provenance & Evidence