Acetic Acid → 5-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde

HRID 1523955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523955
C1N2CN3CN(C2)CN1C3.[Br:11][C:12]1[CH:13]=[C:14]2[CH:20]=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1.C[C:22](O)=[O:23]>O>[Br:11][C:12]1[CH:13]=[C:14]2[C:20]([CH:22]=[O:23])=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 247296055-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehydeAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Hexamethylenetetramine (1.08 g, 7.61 mmol) was added to a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1 g, 5 mol) in HOAc (6.34 mL). The mixture was heated at 100° Celsius for 6 hours. The reaction mixture was then cooled to rt and diluted with water. The mixture was extracted with EtOAc, dried (Na2SO4), filtered and concentrated to dryness. The residue was purified by FCC to provide the title compound (379 mg, 33%). 1H NMR (500 MHz, CDCl3) δ 10.02 (s, 1H), 8.77 (d, J=2.2, 1H), 8.48 (d, J=2.2, 1H), 7.99 (d, J=2.7, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to rt
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-b7f931ab8a0a43aa96bc10d808ae11ec
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079866B2

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