Sodium methanethiolate → HCID 86722485, compound

(3R,4aR,12bR)-12b-ethyl-9-(4-fluorophenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-3-ol (11, R1=4-Fluorophenyl, R2=Ethyl, R3=Trifluoromethyl) (0.240 g, 0.538 mmol), sodium methanethiolate (0.188 g, 2.69 mmol) and N,N-dimethylacetamide (12 mL) were heated via microwave at about 90° C. for about 1 h. The reaction mixture was purified without manipulation in two portions by preparative reverse phase HPLC using a Hypersil HS C18 column (250 mm×21.2 mm, 8 μm particle size) with a gradient of 50-100% MeCN in 0.05 N aq. ammonium acetate pH 4.5 buffer. Product fractions were concentrated under reduced pressure then basified with sat. NaHCO3 then extracted with EtOAc. The organic solution was dried over MgSO4, filtered and concentrated under reduced pressure to yield (3R,4aR,12bR)-12b-ethyl-9-(4-(methylthio)phenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-3-ol (11, R1=4-(Methylthio)phenyl, R2=Ethyl, R3=Trifluoromethyl) (0.230 g, 90%); LC/MS, method 3, Rt=2.90 min, MS m/z 475 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.24 (d, J=1.3 Hz, 1H), 7.83 (s, 1H), 7.75-7.68 (m, 2H), 7.57 (s, 1H), 7.48-7.42 (m, 2H), 5.84 (s, 1H), 3.23-3.19 (m, 1H), 2.95-2.90 (m, 1H), 2.54 (s, 3H), 2.27-2.18 (m, 1H), 2.15-1.95 (m, 4H), 1.91-1.76 (m, 2H), 1.70-1.57 (m, 5H), 1.38-1.29 (m, 1H), 0.43 (t, J=7.3 Hz, 3H).