Dimethylformamide → Benzyl (2-methyl-1H-indol-3-yl)acetate

HRID 1591768Notes

Reaction equation

HRID 1591768 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C=O.[CH3:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:26]=[CH:25][CH:24]=2>O>[CH2:7]([O:33][C:31](=[O:32])[CH2:30][C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][C:21]=1[CH3:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5891072-Methyl-1H-indole-3-acetic acid

Product 1

HCID 38336027Benzyl (2-methyl-1H-indol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon gas, potassium carbonate (2.52 g) and benzyl bromide (1.2 mL) were added to dimethyl formamide (20 mL) solution containing 2-(2-methylindol-3-yl)acetic acid (1.73 g), which was stirred at room temperature for 2 hours. The reaction mixture was radiationally cooled and water was added, and then the mixture was extracted by ethyl acetate. The extract was sequentially washed with water and saturated brine and dried by sulfuric anhydride sodium, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give a title compound (2.63 g) having the following physical properties was obtained.

Workup

  1. temperatureThe reaction mixture was radiationally cooled
  2. extractionthe mixture was extracted by ethyl acetate
  3. washThe extract was sequentially washed with water and saturated brine
  4. dry with materialdried by sulfuric anhydride sodium
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-51b8733d373e429083579beb7f6892fa
Source dataset
uspto-grants-2007_11
Patent number
US07291644B2

Reaction notes

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