Sodium Bicarbonate → HCID 59332637, compound

Participants

Reaction Steps

Ethyl 5-bromo-3-(2,6-dimethyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate (0.212 g, 0.535 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (13 mL). A solution of 0.0004M EDTA (3.61 mL, 0.0014 mmol) was added followed by the portion-wise addition of a suspension of Oxone (0.986 g, 1.60 mmol) and Sodium bicarbonate (0.449 g, 5.35 mmol), in 3 mL water. The reaction was stirred overnight at room temperature. An Oxone/sodium bicarbonate solution in the same amounts as above was added to the reaction and stirred for 3 hours. The reaction was diluted with water and dichloromethane. The organic layer was washed 2× water. The combined aqueous layers were backextracted with dichloromethane. The combined organics were washed with water, brine, dried with MgSO4, concentrated. The crude compound was purified by Combiflash silica column chromatography using 0-5% Ethylacetate/dichloromethane on silica to give 0.189 g (82%) of the title compound.

Provenance & Evidence