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

HRID 627787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627787
[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-2992a21b4465400aa7c0077fbcbe2723
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309250B2

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