Phosphorus oxychloride → HCID 90040707, compound

Participants

Reaction Steps

To a solution of (S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (200 mg, 721 μmol, Eq: 1.00) and 2,6-difluoroaniline (121 mg, 101 μL, 938 μmol, Eq: 1.3) in pyridine (2 mL) at 0° C. was added dropwise phosphorus oxychloride (166 mg, 101 μL, 1.08 mmol, Eq: 1.5). The cooling bath was removed and the reaction stirred at RT overnight. The reaction mixture was concentrated in vacuo and water was added to the residue. The resulting mixture was extracted with EtOAc and the combined organic layers were washed with 0.1 M HCl, 0.1 M NaOH, and brine and concentrated in vacuo. The crude material was purified by flash chromatography to give (S)-tert-butyl 3-(2,6-difluorophenylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate as a colorless oil (90 mg), m/z=411 (M+Na).

Provenance & Evidence