Potassium Carbonate → ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

HRID 38491Notes

Reaction equation

HRID 38491 reaction equation
C([O-])([O-])=O.[K+].[K+].C([O:10][C:11]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[CH:25]1[CH2:27][CH2:26]1)(=O)C>CCO>[CH:25]1([N:15]2[C:16]3[C:12](=[C:11]([OH:10])[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=3)[CH:13]=[CH:14]2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57930960ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate

Product 1

HCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

K2CO3 (69.6 g) was added to a solution of ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate (72.3 g) in EtOH (360 ml) placed in a 2 L flask and the mixture was stirred at room temperature for 4 h. EtOH was evaporated and the redisue was diluted with EtOAc. The mixture was washed with water and brine, dried over Na2SO4. After filteration and concentration, the residue was triturated with toluene and hexane to give intended compound as a pale tan solid.

Workup

  1. customplaced in a 2 L flask
  2. customEtOH was evaporated
  3. additionthe redisue was diluted with EtOAc
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter filteration and concentration
  7. customthe residue was triturated with toluene and hexane
  8. customto give

Sources & evidence

ORD record
ord-576af9076b4f4f84bee43397b7edbf15
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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