Sodium Hydroxide → [1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetic acid

HRID 1451535Notes

Reaction equation

HRID 1451535 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([O:24]C)=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.CCOCC.CCCCCC>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53800337Methyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetate

Product 1

HCID 19041685[1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To the methyl ester from Step 7 (1.63 g, 3.68 mmol) in 20 mL of methanol was added 5 mL of 2N NaOH, and the mixture was heated to reflux for 2 h then cooled. The reaction mixture was partitioned between ethyl acetate and 1M HCl. The organic layer was washed with brine, dried over MgSO4 and evaporated to give a solid. This material was swished twice in 15% ether/hexane to provide 1.23 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperaturethen cooled
  4. customThe reaction mixture was partitioned between ethyl acetate and 1M HCl
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a solid

Sources & evidence

ORD record
ord-2cfd5522bbad4582b830604fd9c9f0e7
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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