Ethyl 4-bromobutyrate → Ethyl 4-(3-benzyloxycarbonyl-1-indolyl)-butyrate

HRID 260833Notes

Reaction equation

HRID 260833 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:2]1.Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:13]([O:12][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:2]=1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 76300Ethyl 4-bromobutyrateHCID 8605861benzyl 1H-indole-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22400494Ethyl 4-(3-benzyloxycarbonyl-1-indolyl)-butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of benzyl indole-3-carboxylate, ethyl 4-bromobutyrate and potassium t-butoxide in N,N-dimethylformamide was stirred at 50° C. for 4 hours. After insoluble materials were filtered off, the filtrate was diluted with ethyl acetate, and washed with diluted hydrochloric acid and water, dried over magnesium sulfate and concentrated. The concentrate was chromatographed on a silica gel column to give the object compound.

Workup

  1. filtrationAfter insoluble materials were filtered off
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with diluted hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on a silica gel column
  7. customto give the object compound

Sources & evidence

ORD record
ord-bea85c6851bd439881b44c9c5a4c9fcc
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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