Sodium Pyrosulfite → 1-(4-Cyanophenyl)-2-trifluoromethylimidazo[4,5-c]pyridine

HRID 973472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973472
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.O.[F:18][C:19]([F:23])([F:22])[CH:20]=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C)C(=O)C.C(OCC)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=[C:20]2[C:19]([F:23])([F:22])[F:18])=[CH:10][CH:11]=1)#[N:16]

Komponenten

6

Edukt 3

HCID 656671Sodium PyrosulfiteHCID 27813662,2,2-Trifluoroacetaldehyde hydrateHCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridine

Produkt 1

HCID 150053981-(4-Cyanophenyl)-2-trifluoromethylimidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (420 mg, 2.0 mmol) (prepared as above), trifluoroacetaldehyde hydrate (232 mg, 2.0 mmol), and sodium metabisulphite (475 mg, 2.5 mmol) in N,N-dimethylacetamide (10 ml) was heated under reflux for 16 hours. After being cooled, the mixture was diluted with ethyl acetate (200 ml), washed with saturated aqueous sodium bicarbonate (50 ml) and water (5×50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with ethyl acetate) to give 1-(4-cyanophenyl)-2-trifluoromethylimidazo[4,5-c]pyridine, 337 mg.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter being cooled
  4. washwashed with saturated aqueous sodium bicarbonate (50 ml) and water (5×50 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (eluting with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-472c4f40713c4985abed09505898e46c
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05063237

Notizen zur Reaktion

Wird geladen…