[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[F:18])[CH:9]=2)[NH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1.O>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]([F:18])=[CH:13][CH:14]=[CH:15][C:16]=3[F:17])[CH:9]=2)[N:4]([CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][O:30]2)[N:3]=1
To a solution of 3-bromo-5-(2,6-difluoro-phenyl)-1H-indazole (30.0 g, 97.05 mmol) and p-toluene sulfonic acid (3.7 g, 19.4 mmol) in THF (776 ml) was added 3,4-dihydro-2H-pyran (18.2 ml, 194.1 mmol) at RT. The mixture was stirred at 70° C. for 8 h. The reaction mixture was cooled to RT. Water was added to the reaction mixture and extracted with EtOAc (2×200 ml). The organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure. The crude product was purified by column using (100-200 mesh) silica with 0-5% EtOAc in hexane to provide 3-bromo-5-(2,6-difluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-indazole (18.5 g, 48.4% yield). MS (ESI, pos. ion) m/z: 393.1 (M+1).
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