[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:20]1[CH2:22][CH2:21]1)=[N:5][N:6]2[CH2:11][C:12]1[N:17]=[C:16]([CH3:18])[C:15]([OH:19])=[CH:14][CH:13]=1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].N1C=CN=C1>CN(C=O)C>[Si:27]([O:19][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[C:2]([NH2:1])[C:3]=3[C:4]([CH:20]3[CH2:22][CH2:21]3)=[N:5]2)=[N:17][C:16]=1[CH3:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28]To 6-((4-amino-3-cyclopropyl-1H-indazol-1-yl)methyl)-2-methylpyridin-3-ol (100 mg, 0.340 mmol) in DMF (5 mL) was added tert-butylchlorodimethylsilane (66.6 mg, 0.442 mmol) and 1H-imidazole (116 mg, 1.70 mmol). The reaction mixture was stirred for 18 hours at ambient temperature. The solvent was removed under reduced pressure, and the residue was purified by silica gel flash chromatography (1:4 EtOAc/hexanes) to give final product (97%).
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