Sodium Bicarbonate → HCID 59332637, compound

HRID 656034Notes

Reaction equation

HRID 656034 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][CH:20]([CH3:22])S[CH:18]([CH3:23])[CH2:17]1.O[O:25][S:26]([O-:28])=O.[K+].C(=O)(O)[O-].[Na+].OOS([O-])=O.[K+].C(=O)(O)[O-].[Na+]>COCCOC.O.ClCCl.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=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[CH2:17][CH:18]([CH3:23])[S:26](=[O:28])(=[O:25])[CH:20]([CH3:22])[CH2:21]1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59332633HCID 59332633, compoundHCID 86641892HCID 86641892, compound

Product 1

HCID 59332637HCID 59332637, compoundYield 82.5%

Reagents, catalysts & solvents 4

HCID 6049Ethylenediaminetetraacetic AcidCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  1. stirringstirred for 3 hours
  2. washThe organic layer was washed 2× water
  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-b79a6997a06b494da44728e6a3b26c63
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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