1
718
D. A. Alonso et al.
PRACTICAL SYNTHETIC PROCEDURES
Di(3-pyridyl)acetylene (16)36
(13) (a) Beletskaya, I. P.; Kashin, A. N.; Karlstedt, N. B.; Mitin,
A. V.; Cheprakov, A. V.; Kazankov, G. M. J. Organomet.
Chem. 2001, 622, 89. (b) Iyer, S.; Ramesh, C. Tetrahedron
Lett. 2000, 41, 8981. (c) Iyer, S.; Jayanthi, A. Tetrahedron
Lett. 2001, 42, 7877. (d) Iyer, S.; Jayanthi, A. Synlett 2003,
1125.
A reaction tube of the carousel reaction equipment, was charged
with 3-iodopyridine (14, 0.42 g, 2 mmol), decane (0.39 mL, 2
mmol), bis(trimethylsilyl)acetylene (15, 0.27 mL, 1.2 mmol), pyr-
rolidine (0.51 mL, 6 mmol), CuI (19.4 mg, 0.1 mmol), 1 (4.069 mg,
0
.005 mmol, 0.5 mol% Pd) and NMP (4 mL). The mixture was
stirred at 110 ºC in air and the reaction progress was analyzed by
GLC. To the crude reaction mixture water was added and was ex-
(14) Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem.
1996, 61, 2346.
tracted with EtOAc (3 × 25 mL) and washed with H O (3 × 15 mL).
(15) Costa, A.; Nájera, C.; Sansano, J. M. J. Org. Chem. 2002, 67,
5216.
2
The organic phase was dried with MgSO and evaporated (15 mm
4
1
Hg) to afford the crude product 16 (>95% pure by H NMR) (0.15
(16) 4-Biphenylacetic acid(felbinac) and the salt of 2-ethyl-4-
biphenylacetic acid with dimethylaminoethanol(nam-
oxyrate) are anti-inflammatory and analgesic drugs,
respectively: USP Dictionary of USAN and International
Drugs Names 98; U.S. Pharmacopeia: Rockville, 1997.
g, 85%); mp 57–59 ºC (EtOAc); R 0.50 (EtOAc).
f
–
1
IR (film): 3049, 3038 cm .
1
H NMR: d = 7.30 (dd, J = 7.95, 4.83 Hz, 2 H), 7.83 (dt, J = 7.95,
1
.71 Hz, 2 H), 8.58 (dd, J = 4.83, 1.23 Hz, 2 H), 8.79 (br s, 2 H).
(
(
(
17) Baleizao, C.; Corma, A.; García, H.; Leyva, A. Chem.
Commun. 2003, 606.
18) Luo, F.-T.; Jeevanandam, A.; Basu, M. K. Tetrahedron Lett.
1
3
C NMR: d = 89.0, 119.5, 122.9, 138.3, 148.8, 152.0.
MS: m/z (%) = 181 (14), 180 (100), 179 (26), 152 (11), 127 (18),
00 (10), 98 (10), 74 (20).
1998, 39, 7939.
1
19) Pacheco, M. C. Oxime-derived Palladacycles as Catalysts in
Carbon-Carbon Bond Forming Reactions., Ph.D. Thesis;
Alicante University: Alicante, 2003.
Acknowledgment
(
20) Stanforth, S. P. Tetrahedron 1998, 54, 263.
This work has been supported by the Dirección General de Investig-
ación of the Ministerio de Ciencia y Tecnología (MCyT)
(21) (a) Gray, M.; Andrews, I. P.; Hook, D. F.; Kitteringham, J.;
Voyle, M. Tetrahedron Lett. 2000, 41, 6237. (b) Molander,
G. A.; Yun, C.-S. Tetrahedron 2002, 58, 1465.
(BQU2001-0724-CO2-01). M. C. P. and L. B. thank Generalitat
Valenciana for pre-doctoral fellowships.
(22) (a) Zou, G.; Reddy, Y. K.; Falck, J. R. Tetrahedron Lett.
2001, 42, 7213. (b) Falck, J. R.; Kumar, P. S.; Reddy, Y. K.;
Zou, G.; Capdevila, J. H. Tetrahedron Lett. 2001, 42, 7211.
23) Ramesh, C.; Kubota, Y.; Miwa, M.; Sugi, Y. Synlett 2002,
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