4-Methylmorpholine → Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoate

Participants

Reaction Steps

Ethyl 3-(6-hydroxybenzo[b]thiophen-3-yl)propanoate (100 mg, 0.4 mmol) and 4-methylmorpholine (0.05 ml, 0.44 mmol) were dissolved in THF (5 ml) and stirred for 5 minutes. 2-[6-(Methylamino)-2-pyridyl]ethan-1-ol (91 mg, 0.6 mmol), triphenylphosphine (210 mg, 0.8 mmol) and diisopropyl azodicarboxylate (0.16 ml, 0.8 mmol) were added to the mixture sequentially. After stirring overnight under argon, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate, filtered and evaporated under vacuum. The crude product was chromatographed over silica gel to yield 30 mg (19%) of Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoate.

Provenance & Evidence