Potassium Hydroxide → HCID 9939669, compound

Participants

Reaction Steps

At ambient temperature, to a stirred solution of 5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester (0.722 g, 1.05 mmol) in THF:MeOH (3:2, 10 mL) was added 1N KOH (5.26 mL). After 1.5 h, the reaction was quenched with 1N HCl (40 mL) and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated. Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil, eluting with 25% EtOAc/hexane gave 0.596 g (85%) of the title compound as a white solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.34-1.39 (m, 2 H), 1.49-1.54 (m, 5 H), 1.62-1.73 (m, 3 H), 1.79-1.83 (m, 1 H), 2.43 (s, 3 H), 3.23 (quintet, 1 H), 3.97 (s, 3 H), 7.24 (dd, 1 H), 7.30 (d, 1 H), 7.34-7.36 (m, 2 H), 7.49 (t, 1 H), 7.64 (t, 1 H), 8.19 (d, 1 H), 8.72 (s, 1 H), 13.34 (br. s, 1 H). IR (KBr) 3400, 2950, 1690, 1375 and 860 cm-1. mass spectrum (-ESI), m/z 669/671 (M-H). Anal. Calcd. for C31H27BrO6S3 : C, 55.44; H, 4.05 N, 0.00. Found: C, 55.25; H, 4.11 N, 0.01.

Provenance & Evidence