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

HRID 1749820ノート

反応式

HRID 1749820 の反応式
[C:1]([C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[CH:11][C:6]2=[CH:5][CH:4]=1)#[CH:2].[C:12](O)(=[O:14])C.C1N2CN3CN(C2)CN1C3.C(=O)([O-])O.[Na+]>O>[C:1]([C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[C:11]([CH:12]=[O:14])[C:6]2=[CH:5][CH:4]=1)#[CH:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 516892Sodium BicarbonateHCID 101032716-ethynyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 866820046-ethynyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde収率 85%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

6-Ethynyl-1H-pyrrolo[2,3-b]pyridine (0.016 g, 0.11 mmol) was successively added with acetic acid (0.1 mL), water (0.2 mL), and hexamethylenetetramine (0.023 g, 0.17 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 to obtain 6-ethynyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.016 g, 85%).

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

出典と根拠

ORDレコード
ord-cb5c346b0bfe420e82b0945bdbf30fcb
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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