[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([NH2:35])=[N:5][C:6]2([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([C:29]2[CH:34]=[N:33][CH:32]=[CH:31][N:30]=2)[CH:22]=1)[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1.B(Br)(Br)Br.O.N>C(Cl)Cl>[NH2:35][C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[C:6]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:29]3[CH:34]=[N:33][CH:32]=[CH:31][N:30]=3)[CH:22]=2)([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[N:5]=1To a solution of 4-fluoro-1-(4-methoxy-3-(pyrazin-2-yl)phenyl)-1-(2-(trifluoromethyl) pyridin-4-yl)-1H-isoindol-3-amine (0.65 g, 1.36 mmol) in DCM (12.5 ml), boron tribromide (0.718 ml, 4.20 mmol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 hour and then allowed to reach room temperature. Water (5 ml) was added and the pH was adjusted to approx 8 with aqeuous conc. NH3. The organic phase was separated and aqueous phase was extracted with DCM (20 mL). The combined organic phases were passed through a phase separator (Sorbent) and concentrated under reduced pressure. The residue was purified twice by preparative chromatography to give the title compound (210 mg, 32%).
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