Hydrochloric Acid → 1-[4-(4-Chloro-phenoxy)-phenyl]-5-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of t-butyl nitrite (4.62 mg, 0.045 mmol) in DMF (0.2 mL) is heated to 65° C. while 5-(4-amino-3-trifluoromethyl-phenyl)-1-[4-(4-chloro-phenoxy)-phenyl]-pyrrolidin-2-one (10 mg, 0.022 mmol) in DMF (0.2 mL) is added in dropwise. The resulted mixture is stirred at 65° C. for an extra 5 min and then cooled down to room temperature. The reaction mixture is treated with 2 N HCl (5 mL) and extracted with EtOAc (3×3 mL). The combined organic layers is concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 0˜50%) to provide the title compound 1-[4-(4-chloro-phenoxy)-phenyl]-5-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one as colorless oil (˜7 mg, 72%). 1H NMR (CDCl3, 400 MHz) δ 7.53 (d, 1H), 7.47 (s, 1H), 7.46 (d, 1H), 7.41 (t, 1H), 7.31 (d, 2H), 7.25 (d, 2H), 6.88 (d, 2H), 6.86 (d, 2H), 5.28 (t, 1H), 2.60-2.80 (m, 3H), 1.99-2.02 (m, 1H); HPLC-MS calculated for C23H17ClF3NO2 (M+H+) 432.1, found 432.1.

Provenance & Evidence