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

HRID 68664

Reaktionsgleichung

Reaktionsgleichung von HRID 68664
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ed03bab02a1148a3b6e96aeff5e1af59
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822469B2

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