Isobutyric Acid → HCID 83449983, compound

Participants

Reaction Steps

To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (122 mg) and isobutyric acid (0.056 ml) in DMF (2 ml) was added HATU (242 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. After being stirred, N,N-diisopropylethylamine (0.311 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was stirred in AcOH (2.00 ml) at 90° C. for 1 h and at room temperature overnight. The mixture was quenched with saturated NaHCO3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (119 mg) as a pale yellow solid.

Provenance & Evidence