Benzyl Bromide → 1-Benzyl-2-methyl-1H-indole-3-carboxylic acid

HRID 1865917Notes

Reaction equation

HRID 1865917 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([OH:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([C:11]([OH:13])=[O:12])=[C:2]1[CH3:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 31596712-Methyl-1H-indole-3-carboxylic acid

Product 1

HCID 667434811-Benzyl-2-methyl-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 0.50 g (3.10 mmol) 2-methyl-1H-indole-3-carboxylic acid (described in J. Heterocyclic Chem. 1977, 14, 1123) in 5 ml DMF was added 0.27 g (6.75 mmol) of NaH (60% in oil). The mixture was stirred at RT for 30 min. and then 0.39 ml (3.28 mmol) of benzyl bromid was added. The mixture was stirred an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Crystallization in Et2O afforded 1-Benzyl-2-methyl-1H-indole-3-carboxylic acid.

Workup

  1. stirringThe mixture was stirred an additional hour
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customCrystallization in Et2O

Sources & evidence

ORD record
ord-8ca8254a529b4f8ca6c90968ae563c40
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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