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

HRID 1711333Notes

Reaction equation

HRID 1711333 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 were added 0.27 g (6.75 mmol) of NaH (60% in oil). The mixture was stirred at room temperature for 30 min. and then 0.39 ml (3.28 mmol) of benzyl bromid were added. The mixture was stirred for one 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 from Et2O afforded 1-benzyl-2-methyl-1H-indole-3-carboxylic acid.

Workup

  1. stirringThe mixture was stirred for one 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 from Et2O

Sources & evidence

ORD record
ord-ed37d7a142614c5e9211138102733477
Source dataset
uspto-grants-2010_09
Patent number
US07790752B2

Reaction notes

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