Hydrochloric Acid → HCID 15981403, compound

Participants

Reaction Steps

Concentrated HCl (0.5 mL) was added dropwise to a stirred solution of 2-(2-fluoro-5-phenyl-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester (113 mg, 0.29 mmol, 1.0 eq.) in dioxane (6 mL) and water (2 mL). The reaction was heated at reflux overnight. The reaction was cooled to ambient temperature and the solvent removed in vacuo. The crude residue was partitioned between water (10 mL) and EtOAc (15 mL) and the aqueous layer extracted with EtOAc (3×15 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography on SiO2, eluting with 50% EtOAc/petroleum ether to 100% EtOAc to 10% MeOH/DCM to give the desired product as a yellow solid (25 mg, 0.09 mmol, 30%).

Provenance & Evidence