Cesium carbonate → N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)-N-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-b]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Trimethylsilylethoxymethyl chloride (0.13 g, 0.81 mmol) was added to a solution of N-(3-bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide (0.29 g, 0.62 mmol) and cesium carbonate (0.61 g, 1.8 mmol) in DMF (6.2 mL) at 0° C. The reaction mixture was gradually warmed to 23° C. and stirred for 2 h, then partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 18% ethyl acetate in petroleum ether to give the title compound. MS: m/z=600.2 (M+1).

Provenance & Evidence