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

HRID 1749820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749820
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cb5c346b0bfe420e82b0945bdbf30fcb
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156827B2

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