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

HRID 1523955ノート

反応式

HRID 1523955 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b7f931ab8a0a43aa96bc10d808ae11ec
出典データセット
uspto-grants-2015_07
特許番号
US09079866B2

反応ノート

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