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

HRID 1251276Notes

Reaction equation

HRID 1251276 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-d200a607d40c43e9a3664288e381fc14
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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