Tetrahydrofuran → HCID 16051656, compound

Participants

Reaction Steps

A 3 N aqueous KOH solution (2 mL) was added to a solution of 2-fluoro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester (14.4 mg, 0.03 mmol, 1 equiv.) in 2:1 tetrahydrofuran:methanol (3 mL) and the mixture was shaken for 16 hours. The mixture was concentrated under a stream of N2 and the pH adjusted to 1 with 3 N aqueous HCl solution (2 mL). The mixture was extracted with 1:1 CHCl3:IPA (3×1 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed under reduced pressure to afford 2-fluoro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, 12 mg (86% yield). LC @215 nm; Rt 2.27: 98%, m/z (ES+): 539 (M+H+.); δH (400 MHz; d6-Acetone) 10.69 (1H, br. s), 8.03 (2H, m), 7.90 (1H, d), 7.86-7.81 (3H, m), 7.82-7.72 (2H, m), 7.50 (1H, d), 7.21 (1H, s), 3.98 (2H, t), 3.74 (3H, s), 2.82 (2H, t).

Provenance & Evidence