Sodium Carbonate → HCID 178498259, compound

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Reaction Steps

A solution of methyl 2-(4-bromobenzyl)-7-methoxy-3H-benzimidazole-4-carboxylate [0.268 g, Reference Example 3(l)] in toluene (8 ml) was treated with tetrakis(triphenylphosphine) palladium (0) (0.266 g), aqueous sodium carbonate solution (0.5 ml, 2M) and diethyl (3-pyridyl)borane (0.085 g). The mixture was heated at reflux for 12 hours then cooled to room temperature. Aqueous work-up and subjected to flash chromatography on silica to give the title compound (0.128 g). NMR {(CD3)2SO}: δ 3.90(s,3H), 4.10(s,3H), 4.40(s,2H), 6.70(d,1H), 7.45(d,3H), 7.60(d,3H), 7.90 (dd,1H), 8.60(d,1H), 8.85(d,1H), 0.10(s,1H).

Provenance & Evidence