Citric Acid → HCID 57863356, compound

Participants

Reaction Steps

The above Compound 10 (400 mg, 0.7 mmol) and palladium acetate (8 mg, 0.035 mmol) were solved in dimethylformamide (11 ml), added with methanol (0.29 ml, 7.16 mmol) followed by triethylamine (0.30 ml, 2.15 mmol), and deaeration of the reaction vessel with carbon monoxide was repeated three times. Then the solution was stirred at room temperature in the presence of carbon monoxide. After 6 hours, the reaction mixture was added with ethyl acetate (40 ml), water (30 ml), an 10% citric acid (4 ml), and shaken for separation. Then the aqueous phase was extracted once with ethyl acetate, and the ethyl acetate phase was washed twice with water, dried over sodium sulfate and subjected to distillation under reduced pressure. The obtained residue (0.38 g) was subjected to silica gel chromatography, to give crystalline 8-benzyloxy-3-(4-fluorobenzyl)-7-(2-methoxyethylcarbamoyl)[1,6]naphthyridine-5-carboxylic acid methyl ester 11 (296 mg, 84.1%).

Provenance & Evidence