Citric Acid → HCID 68359760, compound

Participants

Reaction Steps

To Compound 10 (286 mg, 0.5 mmol) and tetrakistriphenyl phosphine palladium (30 mg, 0.026 mmol) was added a dimethylformamide (4 ml) solution of 2-((E)-3-methoxy-propenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (142 mg, 0.65 mmol), followed by an aqueous solution of 2 moles of potassium carbonate (0.66 ml, 1.32 mmol), and after vacuum deaeration under stirring at room temperature, and replacement with nitrogen, the reaction was heated under stirring in an oil bath at 100° C. After 3 hours, to the reaction mixture were added and dissolved ethyl acetate and water, and was added 10% citric acid (8 ml), and then the mixture was shaken for separation, washed twice with water, dried over sodium sulfate, and subjected to distillation under reduced pressure. The residue was subjected to high flash column chromatography (toluene:acetone (4:1)), and the obtained residue (170 mg) was crystallized from diisopropyl ether, to give 8-benzyloxy-3-(4-fluorobenzyl)-5-(3-methoxypropenyl)[1,6]naphthyridine-7-carboxylic acid (2-methoxyethyl)amide b-11 (135 mg) in 52.3% yield.

Provenance & Evidence