1-Hydroxybenzotriazole → HCID 66854393, compound

Participants

Reaction Steps

A mixture of 4-boronobenzoic acid (500 mg, 3.01 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (866 mg, 4.52 mmol) and 1-hydroxybenzotriazole (554 mg, 3.62 mmol) in acetonitrile (25 mL) was sonicated until it became a solution. N,N-Diisopropylethylamine (1.579 mL, 9.04 mmol) and 3,3-difluoropyrrolidine (484 mg, 4.52 mmol) were added. After 30 min at room temperature, the mixture was quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (3×). The combined extracts were washed with brine, water, dried (Na2SO4) and concentrated. Reverse phase HPLC purification gave the expected product (0.250 mg, 33% yield). MS (ES+) m/z: 256 (M+H); LC retention time: 1.87 min (analytical HPLC Method A).

Provenance & Evidence