Water → 6-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

HRID 1620408Notes

Reaction equation

HRID 1620408 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7](/[CH:13]=C/N(C)C)[N:6]=1.O.I([O-])(=O)(=O)=[O:25].[Na+]>C1COCC1>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH:13]=[O:25])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 86664562(E)-6-(2,4-Difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile

Product 1

HCID 848198116-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT, to the product of step 2 above in THF (70.00 mL) and water (70.00 mL) was added sodium periodate (8.9 g, 42 mmol) in one portion and the reaction mixture was allowed to stir at RT for 2 h, resulting in the formation of a yellow suspension. The suspension was passed through a flitted funnel, washing with THF (2×10 mL). The filtrate was concentrated under reduced pressure and the remaining mixture was extracted with DCM (2×30 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. Purification on the ISCO (40 g column, 20-60% EtOAc in hexanes) afforded 6-(2,4-difluorophenoxy)-2-formylnicotinonitrile as a light yellow crystalline solid. MS (ESI, pos.ion) m/z: M+1=261.0

Workup

  1. customresulting in the formation of a yellow suspension
  2. customThe suspension was passed through a flitted funnel
  3. washwashing with THF (2×10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionthe remaining mixture was extracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on the ISCO (40 g column, 20-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-89bca07b03de484bbddf0e28ee5344bf
Source dataset
uspto-grants-2014_07
Patent number
US08772481B2

Reaction notes

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