Acetone → 1-phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone

HRID 1677402

Reaction equation

HRID 1677402 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[N:11]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:41].CC(C)=O>S([O-])([O-])(=O)=O.[Hg+2].O>[C:1]1([C:7](=[O:41])[CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=4)[N:16]=3)[N:11]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=3)(=[O:32])=[O:31])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 595406337-phenylethynyl-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 595410061-phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanoneYield 61.8%

Reagents, catalysts & solvents 2

HCID 24544Mercuric sulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

7-Phenylethynyl-5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (154 mg, 0.29 mmol), mercury(II) sulfate (127 mg, 0.43 mmol), concentrated sulfuric acid (0.031 ml, 0.58 mmol) and 3 ml of a 3:1 mixture of acetone and water were added to a 5 ml microwave vial. The reaction was heated in a microwave reactor at 110° C. for one hour. The solvent was evaporated and ethyl acetate and aqueous sodium carbonate were added to the residue. The aqueous layer was removed using a reparatory funnel, the organic layer was washed with water twice, then dried and concentrated. The residue was purified by flash chromatography using a gradient of 0% ethyl acetate in hexanes up to 30% to give 100 mg of 1-phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone as the major product. MS: (M+H)+=558.

Workup

  1. additionwere added to a 5 ml microwave vial
  2. customThe solvent was evaporated
  3. additionethyl acetate and aqueous sodium carbonate were added to the residue
  4. customThe aqueous layer was removed
  5. washthe organic layer was washed with water twice
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e3c1f3e308244fa99f00fc54b8056399
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Linked notes

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