C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([OH:25])[CH:23]=3)[CH:18]=[N:17]2)=[CH:12][CH:11]=1.C1COCC1.O>CCOC(C)=O>[Br:8][C:23]1[C:22]([OH:25])=[CH:21][CH:20]=[C:19]2[C:24]=1[N:16]([C:13]1[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=1)[N:17]=[CH:18]2NBS (16.2 g, 91 mmol) was added in one portion to a solution of 1-(4-fluorophenyl)-1H-indazol-6-ol (96, R1=4-Fluorophenyl) (20.3 g, 89 mmol) and THF (500 mL) under a nitrogen atmosphere at about 0° C. After about 1 h, water (500 mL) and EtOAc (400 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (100 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was slurried in DCM (50 mL) then collected by filtration rinsing with DCM (4×25 mL). The solid was dried to afford 7-bromo-1-(4-fluorophenyl)-1H-indazol-6-ol (97, R1=4-Fluorophenyl) (17.2 g, 63% yield) as a faint orange solid. LC/MS, method 3, Rt=2.02 min, MS m/z 307 and 309 (M+H)+. 1H NMR (400 MHz, DMSO) δ 10.52 (d, J=0.9 Hz, 1H), 8.20 (d, J=0.9 Hz, 1H), 7.67 (dd, J=8.6, 0.9 Hz, 1H), 7.54-7.47 (m, 2H), 7.38-7.29 (m, 2H), 6.95 (dd, J=8.6, 0.9 Hz, 1H).
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