2-Bromobenzoic acid → 4-(2-Bromo-benzoyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

DIPEA (460 mg, 0.63 mL, 3.68 mmol) was added dropwise to 2-bromo-benzoic acid (370 mg, 1.84 mmol) in DMF (4 mL). This was followed by the addition of EDCI (423 mg, 2.2 mmol) and HOBT (298 mg, 2.2 mmol). After 2 minutes of stirring, [1,4]diazepane-1-carboxylic acid tert-butyl ester (150 mg, 0.47 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 500 mg (71.12% yield) of 4-(2-bromo-benzoyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Provenance & Evidence