Ethyl Acetate → 3-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)-but-2-enoic acid methyl ester

HRID 1394623Notes

Reaction equation

HRID 1394623 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4]P(OCC)(OCC)=O.CC(C)([O-])C.[K+].[C:20]1([S:26]([N:29]2[C:37]3[C:32](=[C:33]([Br:38])[CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:39](=O)[CH3:40])(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[C:39]([C:30]1[N:29]([S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:27])=[O:28])[C:37]2[C:32]([CH:31]=1)=[C:33]([Br:38])[CH:34]=[CH:35][CH:36]=2)[CH3:40]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 66113Methyl diethylphosphonoacetateHCID 179528101-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)ethanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 692210343-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)-but-2-enoic acid methyl esterYield 769.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyldiethylphosphonoacetate (366 mg, 0.97 mmol) was dissolved in DMF (8 mL) under nitrogen, cooled in an ice bath, and treated with potassium t-butoxide (434 mg, 3.87 mmol). The ice bath was removed and allowed to warm to room temperature over 30 min. 1-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)ethanone (366 mg, 0.97 mmol) dissolved in DMF (4 mL) was added and the reaction heated at 50° C. for 1.5 h. The reaction was allowed to cool and poured into ethyl acetate/saturated ammonium chloride solution. The aqueous was washed with more ethyl acetate. Then the pH was lowered and the aqueous washed a third time with ethyl acetate. The organic portions were washed with brine, dried (MgSO4), filtered and evaporated to give 3.24 g brown oil. The material was purified by column chromatography using (5:1) hexane:ethyl acetate to give 207 mg (28%) of a crude foam. The material was used without further purification. MS [EI+] 434, 436 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. additionwas added
  4. temperaturethe reaction heated at 50° C. for 1.5 h
  5. temperatureto cool
  6. washThe aqueous was washed with more ethyl acetate
  7. washthe aqueous washed a third time with ethyl acetate
  8. washThe organic portions were washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-4e1634bd456e4ea59977d4070aff229c
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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