I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[N:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[N:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>C1COCC1.CCO.O>[N:22]1[CH:27]=[C:26]([C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[O:6])[CH:25]=[N:24][CH:23]=1
A mixture of 3-iodo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 1.1, 550 mg, 1.351 mmol), pyrimidin-5-ylboronic acid (418 mg, 3.38 mmol), Na2CO3 (716 mg, 6.75 mmol), DME (6304 μL), water (1801 μL) and EtOH (901 μL) was stirred at 80° C. for 1 h. THF (5 mL) was added and the mixture was treated with Si-Thiol (938 mg, 1.351 mmol), stirred for 2 h and filtered through Florisil®. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by flash chromatography (Biotage Silica gel column, 25 g, cyclohexane/EtOAc, from 20% to 75% EtOAc) to yield the title compound as a white solid. UPLC-MS (Condition 1) tR=360.0 [M+H]+, m/z=358.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.40 (m, J=8.3 Hz, 2H) 7.72 (t, 1H) 7.91 (m, J=8.6 Hz, 2H) 7.98-8.11 (m, 2H) 8.36 (br. s, br. s, 1H) 9.19-9.31 (m, 3H) 10.52 (br. s, br. s, 1H).
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