Reaction SMILES: [Br:1][C:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:8]=[CH:7][C:6]=2[CH:5]=[C:4]2[C@@:18]3([C:28]#[N:29])[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][C@@H:19]3[CH2:20][CH2:21][O:22][C:3]=12.[Br:30][C:31]1[C:39]2[N:38]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)[N:37]=[CH:36][C:35]=2[CH:34]=[C:33]2[C@:47]3([C:57]#[N:58])[CH2:55][CH2:54][C:53](=[O:56])[CH2:52][C@H:48]3[CH2:49][CH2:50][O:51][C:32]=12.[F-].[Cs+].[F:61][C:62]([Si](C)(C)C)([F:64])[F:63].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O.O.COCCOC>[Br:1][C:2]1[C:10]2[N:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:8]=[CH:7][C:6]=2[CH:5]=[C:4]2[C@@:18]3([C:28]#[N:29])[CH2:26][CH2:25][C@@:24]([OH:27])([C:62]([F:64])([F:63])[F:61])[CH2:23][C@@H:19]3[CH2:20][CH2:21][O:22][C:3]=12.[Br:30][C:31]1[C:39]2[N:38]([C:40]3[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=3)[N:37]=[CH:36][C:35]=2[CH:34]=[C:33]2[C@:47]3([C:57]#[N:58])[CH2:55][CH2:54][C@:53]([OH:56])([C:62]([F:64])([F:63])[F:61])[CH2:52][C@H:48]3[CH2:49][CH2:50][O:51][C:32]=12
Reactant: N#C[C@]12CCC(=O)C[C@@H]1CCOc1c2cc2cnn(-c3ccc(F)cc3)c2c1Br
Reactant: N#C[C@@]12CCC(=O)C[C@H]1CCOc1c2cc2cnn(-c3ccc(F)cc3)c2c1Br
Reactant: C[Si](C)(C)C(F)(F)F
Agent: CCCC[N+](CCCC)(CCCC)CCCC
Agent: [Cs+]
Agent: [F-]
Solvent: COCCOC
Solvent: CCOC(C)=O
Solvent: O
Product: N#C[C@@]12CC[C@](O)(C(F)(F)F)C[C@H]1CCOc1c2cc2cnn(-c3ccc(F)cc3)c2c1Br
Product: N#C[C@]12CC[C@@](O)(C(F)(F)F)C[C@@H]1CCOc1c2cc2cnn(-c3ccc(F)cc3)c2c1Br
Reaction time: 0.25 h
Yield: 68 %

Procedure:
DME (40.0 mL) was added to a mixture of (4aR,12bS)-8-bromo-9-(4-fluorophenyl)-3-oxo-2,3,4,4a,5,6,9,12b-octahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile; compound with (4aS,12bR)-8-bromo-9-(4-fluorophenyl)-3-oxo-2,3,4,4a,5,6,9,12b-octahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile (104, R1=4-Fluorophenyl) and CsF (0.060 g, 0.40 mmol) under a nitrogen atmosphere. After about 15 min, the reaction mixture was cooled to about 0° C. (Trifluoromethyl)trimethylsilane (0.720 mL, 4.87 mmol) was added dropwise over about 5 min. After about 2 h, (trifluoromethyl)trimethylsilane (0.250 mL, 1.69 mmol) was added dropwise. After about 2 h, the volatiles were removed under reduced pressure. The residue was dissolved in THF (40.0 mL). TBAF (1 M solution in THF, 5.00 mL, 5.00 mmol) was added. After about 1 h, the solution was diluted with EtOAc (100 mL) and water (50 mL). The layers were separated and the organic layer was washed with aq. NaCl (50 mL) then dried over Na2SO4, filtered and concentrated under reduced pressure. DCM (5 mL) was added and the solid was collected by filtration rinsing with DCM (2×2 mL) and dried under reduced pressure to afford (3R,4aR,12bS)-8-bromo-9-(4-fluorophenyl)-3-hydroxy-3-(trifluoromethyl)-2,3,4,4a,5,6,9,12b-octahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile; compound with (3S,4aS,12bR)-8-bromo-9-(4-fluorophenyl)-3-hydroxy-3-(trifluoromethyl)-2,3,4,4a,5,6,9,12b-octahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile (105, R1=4-Fluorophenyl, R3=Trifluoromethyl) (1.35 g, 68% yield) as an ivory solid. LC/MS, method 3, Rt=2.36 min, MS m/z 524 and 526 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.36 (s, 1H), 8.09 (s, 1H), 7.62-7.53 (m, 2H), 7.42-7.32 (m, 2H), 6.30 (s, 1H), 4.54-4.43 (m, 1H), 3.59-3.47 (m, 1H), 2.57-2.40 (m, 2H), 2.41-2.29 (m, 1H), 2.25-2.03 (m, 2H), 2.01-1.83 (m, 3H), 1.63-1.51 (m, 1H).