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

HRID 1432322노트

반응식

HRID 1432322 반응식
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

참가 물질

4

반응물 3

HCID 1032Propionic Acid2회HCID 4101Hexamethylenetetramine2회HCID 575955961-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,N-dimethylmethanamine

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e00aa7ed105c4737bfacd752e74fd9fb
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612086B2

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