N-bromobutanimide → 3-Bromo-8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

HRID 449036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449036
[Cl:1][C:2]1[C:3]2[N:4]([CH:8]=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C>[Br:31][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]2=[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[N:9]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 866360348-Chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

Produkt 1

HCID 866360333-Bromo-8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine (2.10 g, 6.5 mmol) in DMF (12 mL) at 0° C. was added NBS (1.40 g, 7.84 mmol) and stirred for 2 h. DMF was removed under pressure and added water (75 mL). Solid formed was extracted with EtOAc (3×50 mL), washed with water (40 mL) and dried (Na2SO4). Evaporation of solvent gave crude material, which was purified by column chromatography on silica gel using CH2Cl2/MeOH (98:2). Yield: 2.05 g (77%); 1H NMR (CDCl3, 300 MHz) δ 7.11-7.21 (m, 5H), 7.28-7.32 (m, 3H), 7.61-7.64 (m, 2H), 7.70 (d, J=2.4 Hz, 1H).

Aufarbeitung

  1. customDMF was removed under pressure
  2. additionadded water (75 mL)
  3. customSolid formed
  4. extractionwas extracted with EtOAc (3×50 mL)
  5. washwashed with water (40 mL)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of solvent
  8. customgave crude material, which
  9. customwas purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3e0d4a4dee4c4cbfa8780af51deba103
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481733B2

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