Lithium Hydroxide → 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylic acid

HRID 387298Notes

Reaction equation

HRID 387298 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:13]([O:15]CC)=[O:14])[CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:18][CH:19]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20]1>CO>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:13]([OH:15])=[O:14])[CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:18][CH:19]1[CH2:23][CH2:22][S:21](=[O:24])(=[O:25])[CH2:20]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59332681Ethyl 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylate

Product 1

HCID 593327835-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of lithium hydroxide (0.64 g, 26.49 mmol) was added to a solution of ethyl 5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxylate (3.52 g, 8.83 mmol) in methanol (100 mL) at room temperature. The mixture was heated at reflux for 1 h and then concentrated. The residue was washed with water, acidified with 1N HCl (pH ˜3), and filtered, giving the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated
  4. washThe residue was washed with water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-79cbf64e1f264825ad5de6121799d5e3
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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