2-Methylphenyl boronic acid → 5-(benzyloxy)-1-o-tolyl-1H-imidazo[4,5-b]pyridine

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Reaction Steps

From 5-(benzyloxy)-3H-imidazo[4,5-b]pyridine and o-tolylboronic acid, prepared in a similar manner as the one described in Example 1.25, Step A, 5-(benzyloxy)-3-o-tolyl-3H-imidazo[4,5-b]pyridine and 5-(benzyloxy)-1-o-tolyl-1H-imidazo[4,5-b]pyridine were obtained, which was then dissolved in DCM and diluted with excess sulfuric acid. The resulting solution was stirred for 30 minutes at room temperature then acidified with the addition of 1 M aqueous hydrochloric acid. The solvent was removed from the organic layer and the residue was purified via preparative HPLC to give the title compound. LCMS m/z=225.9 [M+H]+.

Provenance & Evidence