Sodium Sulfite → Ethyl 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylate

HRID 387297Notes

Reaction equation

HRID 387297 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[CH2:16][CH:17]1[CH2:21][CH2:20]S[CH2:18]1.ClC1C=C(C=CC=1)C(OO)=O.[S:33]([O-:36])([O-])=[O:34].[Na+].[Na+]>ClCCl>[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[CH2:16][CH:17]1[CH2:21][CH2:20][S:33](=[O:36])(=[O:34])[CH2:18]1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 59332587ethyl 5-bromo-3-(tetrahydro-3-thienylmethyl)-1H-indole-7-carboxylate

Product 1

HCID 59332681Ethyl 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylateYield 42.56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-bromo-3-(tetrahydro-3-thienylmethyl)-1H-indole-7-carboxylate (7.61 g, 20.73 mmol) in dichloromethane (150 mL) was added portionwise 3-chlorobenzoperoxoic acid (10.69 g, 62.19 mmol) at room temperature. The resulting solution was stirred for 5 h. Sodium sulfite was added, and the mixture was washed with water, extracted with DCM (3×100 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column on sillal gel (petroleum: ethyl acetate=10:1 to 5:1 to 2:1), giving 3.52 g (42.56%) of the title compound.

Workup

  1. washthe mixture was washed with water
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column on sillal gel (petroleum: ethyl acetate=10:1 to 5:1 to 2:1)

Sources & evidence

ORD record
ord-c887954120f54ac0b585e2bc24d7dd38
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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