Ethyl bromoacetate → 3-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid, ethyl ester

HRID 2233736Notes

Reaction equation

HRID 2233736 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[NH:11][C:10]=2[CH3:19])=[CH:6][CH:5]=1.[CH2:22]([O:24][C:25](=[O:28])[CH2:26]Br)[CH3:23]>CN(C=O)C>[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[N:11]([CH2:26][C:25]([O:24][CH2:22][CH3:23])=[O:28])[C:10]=2[CH3:19])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 117018033-(4-chlorophenoxy)-5-fluoro-2-methyl-1H-indole

Product 1

HCID 116391123-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% disp. in oil) (0.12 g) was added portionwise to a stirred solution of the product from step (i) (0.75 g) in DMF (10 ml) at RT. After 10 min, ethylbromoacetate (345 ul) was added, the mixture stirred at RT for 3 h then quenched with water and extracted with diethylether. The organics were washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 15% ethylacetate/iso-hexane. Yield 0.38 g

Workup

  1. customthen quenched with water
  2. extractionextracted with diethylether
  3. washThe organics were washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with 15% ethylacetate/iso-hexane

Sources & evidence

ORD record
ord-98599851cedc4c0681ce216a1ddf37e1
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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