Dimethylformamide → HCID 21078794, compound

Participants

Reaction Steps

(Cyclopropylmethyl)amine (470 mg, 6.0 mmol), 4-carboxyphenylboronic acid (1.0 g, 6.0 mmol), HOBT (810 mg, 6.0 mmol), HBTU (2.73 g, 7.2 mmol) and DIPEA (1.71 g, 7.2 mmol) were mixed in DMF (10 ml) and stirred at room temperature for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM and aqueous sodium bicarbonate. The organic phase was separated, washed with water and brine and dried (magnesium sulphate). The solvent was evaporated under vacuum and the residue purified on a silica flash column eluting with DCM/ethanol/ammonia (15:8:1 then 10:10:1), to give after evaporation of the solvents 4-[N-(cyclopropylmethyl)aminocarbonyl]phenylboronic acid (300 mg, 23%).

Provenance & Evidence