Acetic Acid → 6-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

HRID 1749815ノート

反応式

HRID 1749815 の反応式
[C:1]1([C:7]2[N:12]=[C:11]3[NH:13][CH:14]=[CH:15][C:10]3=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](O)(=[O:18])C.C1N2CN3CN(C2)CN1C3.C(=O)([O-])O.[Na+]>O>[C:1]1([C:7]2[N:12]=[C:11]3[NH:13][CH:14]=[C:15]([CH:16]=[O:18])[C:10]3=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 516892Sodium BicarbonateHCID 866819996-phenyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 866820006-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde収率 11%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

6-Phenyl-1H-pyrrolo[2,3-b]pyridine (0.10 g, 0.52 mmol) was successively added with acetic acid (0.2 mL), water (0.4 mL), and hexamethylenetetramine (0.11 g, 0.77 mmol), and then the mixture was stirred overnight at 120° C. in a sealed tube. The reaction mixture was cooled to room temperature, and then added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5)) to obtain a solid containing the objective substance. The solid was washed with a mixed solvent of chloroform and methanol to obtain 6-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.013 g, 11%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5))
  7. customto obtain a solid
  8. additioncontaining the objective substance
  9. washThe solid was washed with a mixed solvent of chloroform and methanol

出典と根拠

ORDレコード
ord-da0f7810a96d404db5f28814f6ed8609
出典データセット
uspto-grants-2015_10
特許番号
US09156827B2

反応ノート

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