Water → HCID 58355456, compound

HRID 2169069Notes

Reaction equation

HRID 2169069 reaction equation
[C:1]1([C:7]2[NH:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O[CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:27][O:26][CH2:25][CH2:24][CH2:23][CH2:22][N:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH:9]=[C:10]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 116870064-Methoxybutyl methanesulfonateHCID 12378033Ethyl 5-phenyl-1H-pyrrole-2-carboxylate

Product 1

HCID 58355456HCID 58355456, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 5-phenyl-1H-pyrrole-2-carboxylate (400 mg) and 4-methoxybutyl methanesulfonate (440 mg) were dissolved in DMF (10 ml), cesium carbonate (780 mg) was added and the mixture was stirred at 60° C. for 12 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:9-1:4) was concentrated under reduced pressure to give the object product (430 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (1:9-1:4)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-8889bda071f9485794aa0eec7cfeba5f
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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