Water → 3-[(6-Methylpyridin-2-yl)ethynyl]benzonitrile

HRID 431034Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1 g (8.54 mMol) 2-ethynyl-6-methyl-pyridine (prepared in analogy to D. E. Ames et al., Synthesis, 1981, p. 364-5), 2.3 g (12.8 mMol) 3-bromo-benzonitrile, 0.47 g (0.7 mMol) bis-(triphenylphosphine)-palladium-II-chloride, 80 mg (0.41 mMol) cuprous iodide and 1.53 ml (15 mMol) triethylamine in 10 ml dimethylformamide is stirred for 3 hours at 90° C. The reaction mixture is cooled to ambient temperature, poured into water and extracted with dichloromethane. The organic layer is dried over sodium sulfate, filtered, evaporated to dryness and the residue is purified by chromatography on silica gel with hexane/ethyl acetate (4:1) as eluant. Crystallization from hexane of the obtained product affords 0.53 g (28.4%) of the title compound as brown crystals, melting point 120-3° C.

Workup

temperatureThe reaction mixture is cooled to ambient temperature
extractionextracted with dichloromethane
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
customevaporated to dryness
customthe residue is purified by chromatography on silica gel with hexane/ethyl acetate (4:1) as eluant
customCrystallization from hexane of the obtained product

Sources & evidence

ORD record: ord-b2654aec3105478687c16d90b861636d
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06656957B1

Reaction notes

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