Water → 4-(1-Methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573359ノート

反応式

HRID 573359 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[NH:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:24]([O-])([O-])=O.[Cs+].[Cs+].CI.O>CN(C=O)C>[CH3:24][N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:16]1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866889913-[4-(Benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

生成物 1

HCID 1364090934-(1-Methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of 3-[4-(benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine (300 mg) and Cs2CO3 (649 mg) in DMF (4 mL) was added MeI (0.093 mL) at 0° C. The mixture was stirred at room temperature for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in EtOH (20 mL) and 10% Pd—C (50% wet, 200 mg) was added. The mixture was stirred for 1 h under H2 atmosphere, filtered and evaporated. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (160 mg).

後処理

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOH (20 mL)
  5. addition10% Pd—C (50% wet, 200 mg) was added
  6. stirringThe mixture was stirred for 1 h under H2 atmosphere
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-eab5cf088ed447c7b9b0b8468042a2e4
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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