1,2-Dichloroethane → HCID 86681616, compound

Participants

Reaction Steps

A mixture of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.2 g, 0.476 mmol), 2-(5-methoxy-2,3-dioxoindolin-1-yl)acetic acid (0.112 g, 0.476 mmol), DMAP (0.029 g, 0.238 mmol) and EDC (0.274 g, 1.428 mmol) in DCM (10 ml) was stirred at room temperature overnight. The reaction was washed with 1N HCl, aqueous 5% NaHCO3 and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude was purified by flash chromatography on silica gel (ethyl acetate:DCM=7:3) to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(5-methoxy-2,3-dioxoindolin-1-yl)acetoxy)ethyl)pyridine 1-oxide (0.18635 g, 0.292 mmol, 61% yield). MS/ESI+ 637.19 [MH]+; [αD]=+60.39 c=0.155 in DCM; 1H NMR (300 MHz, DMSO-d6) δ ppm 8.41 (s, 2H), 7.22 (dd, 1H), 7.19-7.21 (m, 1H), 7.18 (d, 1H), 7.06 (d, 1H), 6.89-6.98 (m, 2H), 7.07 (t, 1H), 6.03 (dd, 1H), 4.62 (d, 1H), 4.54 (d, 1H), 3.89 (d, 2H), 3.81 (s, 3H), 3.40 (dd, 1H), 3.21 (dd, 1H), 1.09-1.37 (m, 1H), 0.51-0.67 (m, 2H), 0.28-0.47 (m, 2H)

Provenance & Evidence