Hydrochloric Acid → 2-Bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine

HRID 68664

反応式

HRID 68664 の反応式
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][N:8]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:5]2=[N:6][CH:7]=1.[In].Cl>O1CCCC1.O>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([NH2:11])=[CH:9][N:8]([C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:5]2=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 5359967Indium2 回HCID 866757062-Bromo-7-nitro-5-trityl-pyrrolo[2,3-b]pyrazine

生成物 1

HCID 866757072-Bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2-bromo-7-nitro-5-trityl-pyrrolo[2,3-b]pyrazine (5 g, 10.30 mmol) dissolved in tetrahydrofuran (200.0 mL)/water (50.00 mL) and indium (11.83 g, 103.0 mmol) then HCl (20.60 mL of 6 M, 123.6 mmol) added. Indium dissolves then precipitates out over 5 minutes. Reaction mixture is filtered through celite, washing with EtOAc. Filtrate basified by careful addition of NaHCO3. Emulsion forms and mixture is filtered again before layers separated. Aqueous is extracted with EtOAc. Combined organics dried and concentrated in vacuo to a black foam. Residue is taken up in DCM and purified by chromatography eluting with 0-50% EtOAc—petroleum ether). Product obtained as a green/brown foam. Dried on high vacuum and taken directly on to acylation reaction. (3.43 g, 73%). 1H NMR (400.0 MHz, DMSO) δ 8.46 (s, 1H), 8.40 (s, 1H), 7.38-7.36 (m, H), 7.23-7.20 (m, 8H) and 3.32 (s, 7H) ppm; MS (ES+) 457.0

後処理

  1. customthen precipitates out over 5 minutes
  2. customReaction mixture
  3. filtrationis filtered through celite
  4. washwashing with EtOAc
  5. additionFiltrate basified by careful addition of NaHCO3
  6. filtrationEmulsion forms and mixture is filtered again before layers
  7. customseparated
  8. extractionAqueous is extracted with EtOAc
  9. customCombined organics dried
  10. concentrationconcentrated in vacuo to a black foam
  11. custompurified by chromatography
  12. washeluting with 0-50% EtOAc—petroleum ether)
  13. customProduct obtained as a green/brown foam
  14. customDried on high vacuum
  15. customtaken directly on to acylation reaction

出典と根拠

ORDレコード
ord-ed03bab02a1148a3b6e96aeff5e1af59
出典データセット
uspto-grants-2014_09
特許番号
US08822469B2

関連ノート

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