Allyl bromide → 2-Methylindole-4-acetic acid allyl ester

HRID 11403Notes

Reaction equation

HRID 11403 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([CH2:11][C:12]([OH:14])=[O:13])[C:9]=2[CH:10]=1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+].Cl.C(OCC)(=O)C>CN(C)C=O>[CH2:17]([O:13][C:12](=[O:14])[CH2:11][C:8]1[C:9]2[CH:10]=[C:2]([CH3:1])[NH:3][C:4]=2[CH:5]=[CH:6][CH:7]=1)[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 99205892-Methylindole-4-acetic AcidHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 207296602-Methylindole-4-acetic acid allyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methylindole-4-acetic acid (53 g) in N,N-dimethylformamide (500 ml) was added dropwise allyl bromide (31 ml), and added anhydrous potassium carbonate (59 g). The mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into a mixture of 2N hydrochloric acid-ethyl acetate and then extracted with ethyl acetate. The extraction was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give the title compound (43.5 g) having the following physical data.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe extraction
  4. washwas washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-77ba0c26a98b4db29c2df9d240301f25
Source dataset
uspto-grants-2006_08
Patent number
US07098234B2

Reaction notes

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