C([O:8][C:9]1[C:10](=[O:29])[N:11]([CH:26]([F:28])[F:27])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=2)[CH:14]=1)C1C=CC=CC=1.C(S)C.B(F)(F)F.O(CC)CC>C(Cl)Cl.CO>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:14]=[C:9]([OH:8])[C:10](=[O:29])[N:11]([CH:26]([F:28])[F:27])[CH:12]=2)=[CH:16][C:17]=1[C:22]([F:25])([F:23])[F:24]To a solution of crude 3-(benzyloxy)-5-[4-chloro-3-(trifluoromethyl)phenyl]-1-(difluoromethyl)pyridin-2(1H)-one (58 mg) in CH2Cl2 (1 mL) was added ethanethiol (0.050 mL, 0.675 mmol) then BF3—OEt2 (0.086 mL, 0.675 mmol) at RT. After 3 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 (22 mg, 48%) as an off-white solid. 1H NMR (500 MHz, d6-DMSO): δ 10.12 (s, 1 H); 8.09-7.90 (m, 3 H); 7.82-7.75 (m, 2 H); 7.25 (d, J=2.3 Hz, 1 H). HRMS (ES) calc (M+H)+=340.0158, found 340.0165.
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