Ethanethiol → 1-Isopropyl-3-hydroxy-5-[3-(trifluoromethyl)-4-chlorophenyl]-2(1H)-pyridone

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To a solution of crude 3-(benzyloxy)-5-[4-chloro-3-(trifluoromethyl)phenyl]-1-(propan-2-yl)pyridin-2(1H)-one (86 mg) in CH2Cl2 (1 mL) was added ethanethiol (0.075 mL, 1.019 mmol) then BF3—OEt2 (0.13 mL, 1.026 mmol) at RT. After 5 h the mixture was diluted with MeOH and concentrated. The residue was taken up in DMSO:H2O and purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-70% CH3CN/water over 20 min at 20 mL/min) to give the title compound (24 mg, 36%) as a light tan solid. 1H NMR (500 MHz, d6-DMSO): δ 9.28 (s, 1 H); 7.97 (s, 1 H); 7.92 (dd, J=8.4, 2.2 Hz, 1 H); 7.74 (d, J=8.4 Hz, 1 H); 7.68 (d, J=2.4 Hz, 1 H); 7.14 (d, J=2.4 Hz, 1 H); 5.18-5.11 (m, 1 H); 1.39 (d, J=6.8 Hz, 6 H). HRMS (ES) calc (M+H)+=332.0660, found 332.0661.

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