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

HRID 656017Notes

Reaction equation

HRID 656017 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:20][CH2:19]S[CH2:17]1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.O[O:42][S:43]([O-:45])=O.[K+].C(=O)(O)[O-].[Na+]>COCCOC.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:20][CH2:19][S:43](=[O:45])(=[O:42])[CH2:17]1

Participants

7

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59332573Ethyl 5-bromo-3-(tetrahydro-3-thienyl)-1H-indole-7-carboxylate

Product 1

HCID 59332778Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylateYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a1c4ccf6785f4080a0a7ee3c7f42da26
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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