Dimethylformamide → 1H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-

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Reaction Steps

Sodium hydride (60% suspension in oil, 0.305 g, 7.63 mmol) was added to a stirred solution of 5-bromo-7-azaindole 24 (1.00 g, 5.08 mmol) in DMF (10 mL). After the mixture was stirred for 30 min, 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl; 1.35 mL, 7.63 mmol) was added. The mixture was stirred for 2.5 days and poured into brine and extracted with AcOEt. The organic layer was washed with brine twice, dried (MgSO4), and concentrated. The residue was purified by means of SGC with hexane:AcOEt as eluent to afford 51 (1.50 g, 90%) as a tan syrup. 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.94-0.99 (m, 2H), 3.53-3.61 (m, 2H), 5.71 (s, 2H), 6.53 (d, J=0.36 Hz, 1H), 7.42 (d, J=0.36 Hz, 1H), 8.09 (d, J=0.22 Hz, 1H), 8.42 (d, J=0.22 Hz, 1H).

Provenance & Evidence