benzyl 2,4-bis(benzyloxy)-5-ethyl-6-(6-methoxy-1H-indol-2-yl)nicotinate → 5-ethyl-4-hydroxy-6-(6-methoxy-1H-indol-2-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Participants

Reaction Steps

The intermediate obtained in Step 4 (170 mg, 0.24 mmol) was dissolved in a mixed solvent of MeOH (0.5 mL) and ethyl acetate (2.0 mL) and hydrogenated with 10% Pd on charcoal (50 mg) using a balloon at room temperature. LC/MS showed complete conversion was achieved overnight. The catalyst was filtered over Celite and washed with 5% MeOH in DCM. The filtrate was concentrated to dryness and the residue was triturated with DCM and dried to provide the title compound as a pale yellow powder (27 mg) in 34% yield.

Provenance & Evidence