[H-].[Na+].[F:3][C:4]([F:21])([F:20])[C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[CH2:18][OH:19])=[O:12])[CH2:7][CH2:6]1.Br[C:23]1[CH:24]=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1.O>CS(C)=O>[F:30][C:29]([F:32])([F:31])[C:27]1[CH:26]=[N:25][CH:24]=[C:23]([O:19][CH2:18][C@H:14]2[CH2:15][CH2:16][CH2:17][N:13]2[C:11]([C@H:8]2[CH2:7][CH2:6][C@H:5]([C:4]([F:3])([F:20])[F:21])[CH2:10][CH2:9]2)=[O:12])[CH:28]=1NaH (60% oil dispersant, 11 mg, 0.27 mmol) was placed on the reaction tube, and a solution of [(2R)-1-{[trans-4-(trifluoromethyl)cyclohexyl]carbonyl}pyrrolidin-2-yl]methanol (68 mg, 0.24 mmol, EXAMPLE 31 Step 1) in DMSO (2.0 mL) was added at ambient temperature. After being stirred for 15 min at room temperature, 3-bromo-5-(trifluoromethyl)pyridine (50 mg, 0.22 mmol) was added to the mixture at ambient temperature. The mixture was heated stepwise with continuous stirring, at room temperature for 19 h, at 50° C. for 3 h, at 80° C. for 15 h, and at 100° C. for 15 h. After cooling to room temperature, water was added to the mixture. The mixture was extracted with ethyl acetate twice and washed with brine. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel preparative thin layer chromatography (TLC) (ethyl acetate/hexane 3:2) to afford 40 mg (43%) of the title compound as a colorless viscous oil.
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