Ethylenediaminetetraacetic Acid → Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylate

Ethyl 5-bromo-3-(tetrahydro-3-thienyl)-1H-indole-7-carboxylate (0.670 g, 1.82 mmol) was dissolved in 1,2-dimethoxyethane (50 mL). A solution of 0.0004 M EDTA (10 mL) was added followed by the portion-wise addition of a suspension of Oxone (3.49 g, 5.67 mmol) and Sodium bicarbonate (1.59 g, 18.9 mmol), in water (15 mL). The reaction was stirred for 18 hours at room temperature. Afterwards, the reaction was diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The combined organics were washed with water (2×100 mL). The combined aqueous layers were backwashed with dichloromethane (100 mL). The combined organics were washed with brine, dried with MgSO4, concentrated. The crude compound was purified by Combiflash silica column chromatography using 10% ethyl acetate/dichloromethane on silica to give 0.596 g (82%) of the title compound.

1. extractionextracted with dichloromethane (2×50 mL)
2. washThe combined organics were washed with water (2×100 mL)
3. washThe combined organics were washed with brine
4. dry with materialdried with MgSO4
5. concentrationconcentrated
6. customThe crude compound was purified by Combiflash silica column chromatography

ORDレコード

ord-a1c4ccf6785f4080a0a7ee3c7f42da26

出典データセット

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08071584B2