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

HRID 1432322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432322
C1N2CN3CN(C2)CN1C3.[Br:11][C:12]1[CH:13]=[C:14]2[C:20]([CH2:21]N(C)C)=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1.C(O)(=[O:28])CC>>[Br:11][C:12]1[CH:13]=[C:14]2[C:20]([CH:21]=[O:28])=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1

Komponenten

4

Edukt 3

HCID 1032Propionic Acid2×HCID 4101Hexamethylenetetramine2×HCID 575955961-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,N-dimethylmethanamine

Produkt 1

HCID 247296055-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehydeAusbeute 81 %

Versuchsvorschrift

To a refluxing (oil bath temp. 140° C.) solution of hexamethylenetetramine (8.83 g, 63 mmol) in 66% aqueous propionic acid (31.5 mL) was added a mixture of 5 (16.0 g, 63 mmol) and hexamethylenetetramine (8.83 g, 63 mmol) in 66% propionic acid (47 mL) over 2.5 h. The reflux was continued for 2.5 h, the reaction mixture allowed to cool to room temperature, then poured onto water (220 mL) and the suspension cooled in an ice-bath. The solid was filtered off, washed with ice-cold water (2×), and dried under high vacuum overnight to give 6 as a white solid (11.47 g, 81%); 1H NMR (400 MHz, CDCl3+4 drops d4-MeOH) δ 9.91 (s, 1H), 8.69 (d, J=2.2 Hz, 1H), 8.36 (d, J=2.2 Hz, 1H), 7.95 (s, 1H).

Aufarbeitung

  1. additionpoured onto water (220 mL)
  2. temperaturethe suspension cooled in an ice-bath
  3. filtrationThe solid was filtered off
  4. washwashed with ice-cold water (2×)
  5. customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-e00aa7ed105c4737bfacd752e74fd9fb
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612086B2

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