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Water → 2-Methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo(3,4-b]pyridine

HRID 42572
ノート
印刷プレビュー

反応式

HRID 42572 の反応式
[C:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:10]=[C:9]3[NH:25][N:26]=[CH:27][C:8]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].I[CH3:31].O>CC(C)=O>[CH3:31][N:26]1[CH:27]=[C:8]2[C:9]([N:10]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:25]1.[CH3:31][N:25]1[C:9]2=[N:10][C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]2[CH:27]=[N:26]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 670148534,6-diphenyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

生成物 2

HCID 670142511-Methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine収率 38%HCID 684450762-Methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo(3,4-b]pyridine
収率 47%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

To a suspension of 4,6-diphenyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.10 g, 0.3 mmol, obtained in example 2) in acetone (1 mL), KOH (21 mg, 0.4 mmol) was added under argon atmosphere. Then, a solution of iodomethane (47 mg, 0.3 mmol) in acetone (0.1 mL) was added and stirred overnight at room temperature. Water was added and extracted with CHCl3. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 47 mg of 2-methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 47%) and 38 mg of 1-methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 38%).

後処理

  1. additionwas added under argon atmosphere
  2. extractionextracted with CHCl3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customwas purified by chromatography on silica gel
  7. temperatureof increasing polarity as eluent

出典と根拠

ORDレコード
ord-db921462605e4900b5a92d0579ee40d8
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08536194B2

反応ノート

読み込み中…

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