Cesium carbonate → Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

HRID 2240565Notes

Reaction equation

HRID 2240565 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[CH3:23][O:22][C:20](=[O:21])[CH2:19][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH3:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 27787155-Fluoro-2-methylindole

Product 1

HCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-fluoro-2-methylindole (2.4 g), cesium carbonate (16.6 g) and methyl bromoacetate (5.4 ml) in acetone 240 ml was stirred and heated under reflux for 16 h. The solvent was removed, water and ethyl acetate were added and the organic phase separated. The aqueous phase was re-extraced with ethyl acetate and the combined organic solution dried and concentrated to a solid. Purification by flash chromaography using dichloromethane:ethylacetate gave the subtitle compound as a solid (2.9 g)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. customThe solvent was removed
  4. additionwater and ethyl acetate were added
  5. customthe organic phase separated
  6. customthe combined organic solution dried
  7. concentrationconcentrated to a solid
  8. customPurification by flash chromaography

Sources & evidence

ORD record
ord-bf8ce9aff1814e1b81e38c54708ffab6
Source dataset
uspto-grants-2010_05
Patent number
US07723373B2

Reaction notes

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