C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH3:9].[F:10][C:11]1[C:16]([OH:17])=[CH:15][N:14]=[C:13]2[N:18]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=[CH:20][C:12]=12.O.C(#N)C>CN(C=O)C>[CH2:8]([O:17][C:16]1[C:11]([F:10])=[C:12]2[CH:20]=[CH:19][NH:18][C:13]2=[N:14][CH:15]=1)[CH3:9]Potassium carbonate (3.49 g, 25.3 mmol) and bromoethane (1.10 g, 10.1 mmol) were added to 4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol (2.6 g, 8.43 mmol) in DMF (5 mL). The reaction was heated to 60° C. in a sealed tube for 24 hours and then filtered. After concentration, the filtrate was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, water/ACN, 90/10→10/90, 20CV) to yield 5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridine (360 mg, 12% yield) as a solid.
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