Citric Acid → HCID 59696343, compound

Participants

Reaction Steps

To a dimethylformamide suspension (80 ml) of the above Compound 7 (8.76 g, 20 mmol) were added DBU (4.48 ml, 30 mmol) and benzylbromide (3.56 ml, 30 mmol), and the solution was stirred for 5 hours at room temperature. The reaction solution was added with 0.5M citric acid aqueous solution and 10% sodium hydrogen sulfite aqueous solution, and extracted twice with ethyl acetate. The organic phase was washed with water, saturated sodium hydrogen carbonate and saturated brine. After drying over anhydrous magnesium sulfate, the residue obtained by distilling off the solvent was subjected to silica gel chromatography. The precipitated crystals were collected by filtering, and washed with diisopropyl ether, to give 8-benzyloxy-3-(4-fluorobenzyl)-5-iodo[1,6]naphthyridine-7-carboxylic acid methyl ester 8 (7.64 g) in 72% yield.

Provenance & Evidence