1-Bromopropane → 1-Propylindole-3-carboxylic acid methyl ester

HRID 1699525Notes

Reaction equation

HRID 1699525 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH3:23]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:21][CH2:22][CH3:23])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 699521321-Propylindole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.16 g (1.00 mmol) of indole-3-carboxylic acid methyl ester, 0.5 g (4 mmol) of K2CO3 and 0.5 g (5 mmol) of 1-bromopropane in 10 ml of DMF was stirred at 50° C. overnight. The mixture was partitioned between EtOAc and water. The aqueous phase was extracted with additional EtOAc. The combined organic phases were washed with water, brine and finally dried over Na2SO4 to give crude 1-propylindole-3-carboxylic acid methyl ester.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. extractionThe aqueous phase was extracted with additional EtOAc
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialfinally dried over Na2SO4

Sources & evidence

ORD record
ord-1ae24cb9a40d46a8a7ca9df0b437576b
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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