Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].CCN(C(C)C)C(C)C.O.[OH-].[Li+].[ClH:38]>C(#N)C.O1CCOCC1.O>[ClH:38].[C:8]1([CH:2]([NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:17]([O:16][C:15]([F:14])([F:24])[F:25])[CH:18]=2)[C:3]([OH:5])=[O:4])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Ethyl 2-bromo-2-phenylacetate (400 mg, 1.64 mmol), 3-(trifluoromethoxy)aniline (0.33 mL, 2.47 mmol), and DIPEA (0.43 mL, 2.47 mmol) are dissolved in acetonitrile (5 mL) and heated under MW irradiation at 100° C. for 1 hour (Conversion complete by UPLC/MS-UV). Water (5 mL) and lithium hydroxide hydrate (207 mg, 4.94 mmol) are directly added and the resulting mixture is stirred at RT for 1 hour. Then 4M HCl in dioxane is added until pH 1, the organic solvents are evaporated and the resulting crude oil is purified by filtration through a silica pad using DCM/MeOH=9/1 as the eluent. Intermediate I88 is collected as a brown oil (569 mg, quantitative yield).
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