Phenol → HCID 49806225, compound

Participants

Reaction Conditions

Reaction Steps

Phenol (11.93 mg, 0.127 mmol) was placed in a 2 ml biotage tube, dissolved in tetrahydrofuran (300 μl) and sodium hydride (60%, 5.07 mg, 0.127 mmol) was added. The tube was purged with nitrogen and sealed. After 10 min. a solution of Methyl 2-[4-iodo-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate (50 mg, 0.106 mmol) in tetrahydrofuran (300 μl) was added dropwise and the mixture was heated in a sand bath at 100° C. overnight. After cooling, the mixture was partitioned between water and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane to provide 18 mg (39%) of the title compound as an oil.

Provenance & Evidence