Ethyl chloroformate → HCID 58190515, compound

Participants

Reaction Steps

To a mixture of 3-bromoquinoline-6-carboxylic acid (1.32 g, 5.24 mmol) and TEA (876 uL, 6.29 mmol) in THF (30 mL) was added EtOCOCl (599 uL, 6.29 mmol) at 0° C. and stirred for 30 min. Then, a solution of NaBH4 (793 mg, 21.0 mmol) in H2O (6 mL) was added at the same temperature. The resulting reaction mixture was stirred at 0° C. for 30 min before being warmed to it and stirred overnight. THF was removed. The residue was diluted with H2O, acidified with 4 N HCl, then neutralized with NaHCO3, extracted with EtOAc, and purified by a SiO2 column (0-50% EtOAc/Hexanes, Rf=0.35 in 50% EtOAc) to afford the titled compound as a colorless oil (220 mg).

Provenance & Evidence