Sodium hydride → 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

Into a 50 ml round bottom flask were added 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (1.86 g, 5.78 mmol) and dry tetrahydrofuran (20 ml). The solution was cooled in an ice bath at 0° C. and sodium hydride (305 mg, 60% dispersion in mineral oil, 6.36 mmol) was added in small portions. After 20 minutes, 2-(trimethylsilyl)ethoxymethyl chloride (1.12 mL, 6.35 mmol) was added, and the reaction mixture was allowed to warm to room temperature over 30 minutes. The reaction mixture was allowed stirred at this temperature for an additional 30 minutes. Methanol (1.0 mL) was then added to quench the reaction, followed by the addition of saturated aqueous ammonium chloride solution (10 mL). The mixture was then extracted with dichloromethane (2×20 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to give 2.36 g (90%) 5-bromo-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine as a yellowish oil. 1H-NMR (250 MHz, CDCl3) δ 8.49 (d, J=2 Hz, 1H), 7.84 (d, J=2.25 Hz, 1H), 7.44 (s, 1H), 3.50 (t, J=8.25 Hz, 2H), 0.88 (t, J=8.25 Hz, 2H), −0.08 (s, 9H); MS: m/z 452.9+454.9 (M+H+).

Provenance & Evidence