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

反応式

HRID 1677402 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24544Mercuric sulfate触媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e3c1f3e308244fa99f00fc54b8056399
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

関連ノート

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