Ammonium Chloride → 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

HRID 2409034ノート

反応式

HRID 2409034 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[N:14]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=[CH:12][C:5]2=[N:6][C:7]=1[C:8](=[N:10]O)[CH3:9].[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]2[N:14]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=[CH:12][C:5]2=[N:6][C:7]=1[CH:8]([NH2:10])[CH3:9]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 1364091001-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime

生成物 1

HCID 866898501-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine収率 78.1%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

A mixture of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime (514 mg, 1.41 mmol), Zn power (4.6 g, 70.64 mmol), NH4Cl (1.5 g, 28.26 mmol) in MeOH (20 mL) and HOAc (4 mL) was heated at reflux overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was diluted with CH2Cl2 (200 mL) and aqueous ammonia (20 mL). The organic layer was separated, washed with H2O, dried (NaSO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with MeOH—CH2Cl2 (1:15) to afford 385 mg (78%) of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine as yellow oil. MS (ESI): m/z=350.0 [M+1]+.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. additionThe residue was diluted with CH2Cl2 (200 mL) and aqueous ammonia (20 mL)
  6. customThe organic layer was separated
  7. washwashed with H2O
  8. dry with materialdried (NaSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by SiO2 chromatography
  12. washeluting with MeOH—CH2Cl2 (1:15)

出典と根拠

ORDレコード
ord-df769184f785414ba8ce01e605aea74c
出典データセット
uspto-grants-2014_08
特許番号
US08815877B2

反応ノート

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