[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:5]2=[N:6][CH:7]=1To a 250 ml 3-neck flask, 5-bromo-1H-pyrrolo[2,3-b]pyridine (10 g, 50.5 mmol) and DMF (80 ml) were added. The solution was cool to −40° C. under nitrogen, sodium hydride (1.5 g, 60.6 mmol) was added in 2 batches. The mixture was stirred at −40° C. for 1 hour. Then SEM-Cl (10.7 ml, 60.6 mmol) in DMF (20 ml) was added dropwise and the resulting mixture was allowed to stir at −40° C. for another 2 hours. The reaction was quenched with saturated NH4Cl (40 ml) and worked up with ethyl acetate, brine, dried with Na2SO4. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 5-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (14.4 g, 87% yield). 1H NMR (500 MHz, DMSO-d6) δ 0.02 (s, 9H), 0.92 (m, 2H), 3.59 (m, 2H), 5.72 (s, 2H), 6.65 (s, 1H), 7.84 (s, 1H), 8.37 (2, 1H), 8.45 (s, 1H). MS: m/z 327.0 (M+H+).
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