Br[CH2:2][CH2:3][O:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]1[C:18]([OH:19])=[CH:17][N:16]=[C:15]2[N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=[CH:22][C:14]=12>CN(C=O)C>[F:12][C:13]1[C:18]([O:19][CH2:2][CH2:3][O:4][CH3:5])=[CH:17][N:16]=[C:15]2[NH:20][CH:21]=[CH:22][C:14]=121-Bromo-2-methoxyethane (0.586 g, 4.21 mmol) and potassium carbonate (1.16 g, 8.43 mmol) to 4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol (1.3 g, 4.21 mmol; Example 119, Step A) in DMF (13 mL). The reaction was heated to 65° C. in a sealed tube for 18 hours, cooled down and then filtered. The filtrate was concentrated and purified by reverse chromatography (SP4, 25M, water/ACN 90/10→0/100, 30CV) to yield 4-fluoro-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridine (440 mg, 49.7% yield) as an oil.
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