Dimethylformamide dimethyl acetal → (E)-6-(2,4-Difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile

HRID 1620407Notes

Reaction equation

HRID 1620407 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:13])[N:6]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C=O)C>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7](/[CH:13]=[CH:21]/[N:22]([CH3:24])[CH3:23])[N:6]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 674916176-(2,4-Difluorophenoxy)-2-methylnicotinonitrile

Product 1

HCID 86664562(E)-6-(2,4-Difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(2,4-difluorophenoxy)-2-methylnicotinonitrile (3.40 g, 14 mmol) in N,N-dimethylformamide dimethyl acetal (3.7 mL, 28 mmol) and DMF (5.00 mL) was heated at 140° C. in an oil bath for 18 h. The mixture was concentrated under reduced pressure to remove most of the DMF. The residue containing (E)-6-(2,4-difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile (with some DMF) was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove most of the DMF
  3. additionThe residue containing (E)-6-(2,4-difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile (with some DMF)
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-b025625f3c0747f6881bf5d401bf33ed
Source dataset
uspto-grants-2014_07
Patent number
US08772481B2

Reaction notes

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