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

HRID 1432322ノート

反応式

HRID 1432322 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e00aa7ed105c4737bfacd752e74fd9fb
出典データセット
uspto-grants-2009_11
特許番号
US07612086B2

反応ノート

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