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

HRID 1432322Notes

Reaction equation

HRID 1432322 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e00aa7ed105c4737bfacd752e74fd9fb
Source dataset
uspto-grants-2009_11
Patent number
US07612086B2

Reaction notes

Loading…