Potassium Carbonate → 6-(2-Fluoro-4-formyl-phenoxy)-nicotinonitrile

HRID 228248Notes

Reaction equation

HRID 228248 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].Cl[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[F:10][C:3]1[CH:4]=[C:5]([CH:6]=[O:7])[CH:8]=[CH:9][C:2]=1[O:1][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5872503-Fluoro-4-hydroxybenzaldehydeHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 597302416-(2-Fluoro-4-formyl-phenoxy)-nicotinonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using a method similar to Example 365, step 1, using 4-hydroxy-3-fluoro-benzaldehyde (3.00 g, 21.4 mmol), 6-chloro-nicotinonitrile (2.98 g, 21.5 mmol), and potassium carbonate (7.40 g, 53.5 mmol) in dimethylacetamide (100 mL) after 6 h at 100° C. provides 3.77 g (73%) of the title compound as a yellow solid (silica gel chromatography conditions: 19:1→1:4 hexanes:ethyl acetate): mass spectrum (electrospray): m/z=243.0 (M+1); 1H NMR (CDCl3): 10.00 (d, 1H, J=2.0 Hz), 8.42 (d, 1H, J=1.5 Hz), 8.01 (dd, 1H, J=2.0, 8.3 Hz), 7.80-7.72 (m, 2H), 7.43 (d, 1H, J=7.3 Hz), 7.19 (d, 1H, J=8.8 Hz).

Workup

  1. customafter 6 h
  2. customat 100° C.

Sources & evidence

ORD record
ord-cc529c815b894197b2a7cf2ee33b7036
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

Loading…