Formic Acid → HCID 66781369, compound

Participants

Reaction Conditions

Reaction Steps

8-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline (5.0 g, 11.75 mmol) was slurried in MeOH (117.5 ml). Ammonium formate (7.410 g, 117.5 mmol) and Pd(OH)2/C (0.8252 g, 0.5876 mmol) were added. The reaction mixture was heated to reflux for 2 hours, then cooled to 20° C. Formic acid was added to the slurry until solids went into solution. The mixture was filtered and the filter paper was washed with 10% formic acid in methanol. The filtrate was concentrated to an oil. To the oil was added an excess of NH3 in methanol and resulting the solids were concentrated to dryness. Water was added to the solids and the slurry was stirred for 1 hour (pH was 6.5-7.0 by pH paper). The solids were collected by filtration and then taken up in toluene and concentrated to dryness under vacuum dry for 12 hours to obtain 3.8 g (96% yield) of the desired product.

Provenance & Evidence