Sodium hydride → 6-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine

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Reaction Steps

To a solution of 6-bromo-3H-imidazo[4,5-b]pyridine (1.0 eq.) (see J. Am. Chem. Soc. 1957, 6421.) in DMF (0.2M) was added NaH (1.4 eq.). The mixture was stirred for 30 min then SEM-Cl (2.0 eq.) was added. The final mixture was stirred for 2 h, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with water (3×), brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 7:3) afforded the title compound as a foam.

Provenance & Evidence