Hydrochloric Acid → 2-(4-(5-(4-Chlorophenylsulfonamido)quinolin-6-yloxy)-3-methoxyphenyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To 24.4 (36 mg, 0.1 mmol) and 2,6-lutidine (0.024 mL, 0.2 mmol) in THF (0.5 mL) was added 4-chlorobenzenesulfonyl chloride (26 mg, 0.12 mmol). The mixture was stirred at 70° C. overnight. After cooling, water (1 mL) and 10N NaOH (0.5 mL) were added. The mixture was stirred at room temperature for 5 h. 3N HCl (1.7 mL) and EtOAc were added to the mixture, and the organic layer was separated, dried with MgSO4 and concentrated. Flash column chromatography of the residue afforded 24. MS ESI (pos.) m/z: 499.1 (M+H). 1H NMR (DMSO-d6) δ 10.2 (bs, 1H), 8.82 (d, 1H); 8.50 (d, 1H); 7.92 (d, 1H); 7.71 (d, 2H); 7.61 (dd, 1H); 7.55 (d, 2H); 7.03 (d, 1H); 6.95 (d, 1H); 6.79 (dd, 1H); 6.38 (d, 1H); 3.73 (s, 3H); 3.58 (s, 2H).

Provenance & Evidence