Water → (E)-3-[1-(4-bromomethyl-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 870096Notes

Reaction equation

HRID 870096 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][NH:13][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[Br:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C1COCC1>[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][N:13]([S:25]([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][Br:17])=[CH:24][CH:23]=2)(=[O:26])=[O:27])[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27344094-(Bromomethyl)benzenesulfonyl chlorideHCID 66646340tert-butyl (2E)-3-(1H-pyrrol-3-yl)prop-2-enoate2×

Product 1

HCID 66646385(E)-3-[1-(4-bromomethyl-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.25 g of sodium hydride (60% strength) are suspended in 300 ml of THF under nitrogen at −30° C. 9.78 g of (E)-3-(1H-pyrrol-3-yl)-acrylic acid tert-butyl ester (compound D1) are added to the suspension and warmed slowly to room temperature during 55 min. Afterwards it is recooled to −30° C. and it is added 13.98 g of 4-(bromomethyl)-benzenesulfonylchloride and stirred for 45 min. Then it is warmed to room temperature and stirred for 2 hour. After cooling to 0-5° C. water is added. Then the mixture is extracted with ethyl acetate and the organic phase is dried over sodium sulfate. The organic phase is evaporated under vacuum. The crude product is purified by silica gel flash chromatography using a gradient of hexane and ethyl acetate from 9:1-7:1.

Workup

  1. customis recooled to −30° C.
  2. temperatureThen it is warmed to room temperature
  3. stirringstirred for 2 hour
  4. additionis added
  5. extractionThen the mixture is extracted with ethyl acetate
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. customThe organic phase is evaporated under vacuum
  8. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ead513e52acb4cc599471e20dfdf9899
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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