Ethylenediaminetetraacetic Acid → Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

HRID 656029Notes

Reaction equation

HRID 656029 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[CH2:21][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:43][S:44]([O-:46])=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[CH2:21][CH2:20][CH2:19][S:44](=[O:46])(=[O:43])[CH2:17]1

Participants

7

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59332762Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

Product 1

HCID 59332690Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylateYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate (0.375 g, 1.02 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (25 mL). A solution of 0.0004M EDTA (7 mL) was added followed by the portion-wise addition of a suspension of oxone (1.88 g, 3.05 mmol) and sodium bicarbonate (0.855 g, 10.18 mmol) in 7 mL water. The reaction was stirred for 3 hours at room temperature. The reaction was diluted with water and extracted with dichloromethane. The combined organics were washed with water 2×. The combined aqueous layers were backwashed with dichloromethane. The combined organics were washed with water, brine, dried with MgSO4 and concentrated. The crude compound was purified by Combiflash silica column chromatography using 0-10% ethylacetate/dichloromethane on silica to give 0.290 g (71%) of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organics were washed with water 2×
  3. washThe combined organics were washed with water, 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-ef1a9e66354b4369a79b3716d2fb0846
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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