Water → 4-(4-Methoxyphenylethynyl)-3-cyanopyridine

HRID 1814595Notes

Reaction equation

HRID 1814595 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]#[N:9].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=1.C(N(CC)CC)C.O>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[C:8]#[N:9])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2510201-Ethynyl-4-methoxybenzeneHCID 134111124-Chloro-nicotinonitrile

Product 1

HCID 225032354-(4-Methoxyphenylethynyl)-3-cyanopyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-3-cyanopyridine (1.50 g) and 4-methoxyphenylacetylene (1.60 g) were reacted in the presence of dichlorobistriphenylphosphinepalladium (0.14 g), cuprous iodide (75 mg) and triethylamine (10 ml) in N,N-dimethylformamide (25 ml) in nitrogen atmosphere at 100° C. overnight. The reaction mixture was poured into water (100 ml), and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give 4-(4-methoxyphenylethynyl)-3-cyanopyridine (2.13 g, 95%) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe resulting organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-b3b802698bf5432c85e3388da5fac389
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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