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

HRID 1886173Notes

Reaction equation

HRID 1886173 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-16e2eb1e0d76445790744ac4ffad4cca
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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