Oxalyl chloride → HCID 20773312, compound

Participants

Reaction Steps

Oxalyl chloride (0.35 ml, 4.0 mmol) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (0.58 g, 3.7 mmol) (Method A) in DCM (10 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature for 18 hours and was then added to a solution of 5-(4-methylsulphanylphenylsulphanyl)indoline (1.03 g) (Method B) and 2,6-diphenylyridine (0.84 g, 3.64 mmol) in DCM (20 ml). The mixture was stirred for 16 hours, volatile material was removed by evaporation, and the residue was purified by flash column chromatography on silica gel eluting with 10-20% EtOAc/iso-hexane to give the title compound (0.935 g, 2.3 mmol) as a solid. NMR: 1.80 (s, 3H), 2.50 (s, 3H), 3.11-3.19 (m, 2H), 4.19-4.29 (m, 1H), 4.38-4.47 (m, 1H), 4.86 (s, 1H), 7.19-7.27 (m, 6H), 8.20 (d, 1H); m/z (+ve ESP): 414 (M+H)+.

Provenance & Evidence