Sodium Iodide → 4-((7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide

HRID 2206012ノート

反応式

HRID 2206012 の反応式
C[O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][N:9]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[C:8]=12.[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[O:2]=[C:3]1[C:8]2[N:9]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][NH:4]1

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 1179880834-((7-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide

生成物 1

HCID 1179880844-((7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide収率 98.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-((7-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)benzenesulfonamide (155 mg) in acetonitrile (30 mL) were added sodium iodide (118 mg) and chloro(trimethyl)silane (342 mg), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate). To the obtained residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate and hexane to give the title compound (147 mg).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  3. additionTo the obtained residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-b7d7ba020830409e93758fa78ed0972f
出典データセット
uspto-grants-2016_06
特許番号
US09371320B2

反応ノート

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