[Br:1][C:2]1[C:3]([Cl:12])=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl>CN(C=O)C>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]2[C:10]([I:11])=[CH:9][N:8]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[C:5]2=[N:6][CH:7]=15-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (7.68 g, 21.5 mmol) was dissolved in 100 mL dry DMF and cooled to 0° C. Sodium hydride (60% suspension in mineral oil, 1.03 g, 25.8 mmol) was added cautiously over 5 min. The mixture was cooled to −42° C. and 2-trimethylsilanyl-ethoxymethylchloride (5 mL, 28 mmol) was added slowly over 10 min. The mixture was stirred at −42° C. for 2 h and quenched with 200 mL saturated ammonium chloride solution and 200 mL water. The aqueous mixture was extracted with dichloromethane and the organic phase was washed with water, dried and concentrated to afford 5-Bromo-4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (10.1 g, 20.7 mmol, 96% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.53 (s, 1H), 8.07 (s, 1H), 5.57 (s, 2H), 3.49 (t, J=8 Hz, 2H), 0.79 (t, J=8 Hz, 2H), −0.11 (s, 9H). MS: m/z 486.7/488.7 (M+H+).
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