Br[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:11][C:12]1[C:17]([OH:18])=[CH:16][N:15]=[C:14]2[N:19]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:21][C:13]=12>CN(C=O)C>[F:11][C:12]1[C:17]([O:18][CH:2]([CH3:4])[CH3:3])=[CH:16][N:15]=[C:14]2[N:19]([Si:22]([CH:26]([CH3:28])[CH3:27])([CH:29]([CH3:31])[CH3:30])[CH:23]([CH3:24])[CH3:25])[CH:20]=[CH:21][C:13]=122-Bromopropane (120 mg, 0.973 mmol) and potassium carbonate (448 mg, 3.24 mmol) were added to 4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol (200 mg, 0.648 mmol) in DMF (3 mL). The reaction was heated to 80° C. in a sealed tube for 18 hours and then cooled down. The reaction mixture was concentrated to dryness. The mixture was then suspended in DCM and filtered. The filtrate was concentrated and purified by chromatography (SP4, 12+M, water/ACN 80/20→10/90, 20CV) to yield 4-fluoro-5-isopropoxy-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (65 mg, 42%) as a solid.
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