I. P. Beletskaya et al. / Tetrahedron Letters 44 (2003) 5011–5013
5013
All novel compounds were isolated and characterised
by H NMR and elemental analyses.
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1
Typical procedure: In a flask equipped with a reflux
condenser with an argon inlet 3-iodopyridine (61.5 mg,
0.3 mmol), 4-ethynyl-N,N-dimethylaniline (52.2 mg,
0.36 mmol), potassium carbonate (82.8 mg, 0.6 mmol),
copper(I) iodide (5.7 mg, 30 mmol, 10 mol%) and
Ni(PPh3)2Cl2 (9.8 mg, 15 mmol, 5 mol%) were mixed
under an argon atmosphere in 1.5 mL of dioxane and
0.5 mL of water. The mixture was stirred at reflux for
2 h, then filtered through a pad of silica and evaporated
under reduced pressure. N,N-Dimethyl-4-(3-pyridinyl-
ethynyl)aniline (61.8 mg, 93%) was isolated by column
chromatography. 1H NMR (CDCl3, 400 MHz): 8.72
(1H, m), 8.48 (1H, m), 7.74 (1H, m), 7.40 (2H, m), 7.23
(1H, m), 6.65 (2H, m) 2.99 (6H, s); mp 133°C. Anal.
found: C, 80.98; H, 6.50; N, 12.39. Calcd for C15H14N2:
C, 81.05; H, 6.35; N, 12.60%.
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J. Am. Chem. Soc. 1990, 112, 4324.
Acknowledgements
We are grateful to the Russian Foundation for Basic
Research (Grant 01-03-33144) for financial support.
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