2
998
F. Cardullo et al.
LETTER
Microwave-Assisted Procedure
(3) (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.;
Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.;
Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1
2000, 3815. For the most recent research reports on the
argument see: (b) Ploypradith, P.; Kagan, R. K.; Ruchiravat,
S. J. Org. Chem. 2005, 70, 5119. (c) Gendre, F.; Yang, M.;
Diaz, P. Org. Lett. 2005, 7, 2719. (d) Brenelli, E. C. S.;
Brenelli, J. A.; Pinto, R. C. L. Tetrahedron 2005, 61, 5323.
(e) Ghiron, C.; Nannetti, L.; Taddei, M. Tetrahedron Lett.
2005, 46, 1643. (f) Donati, D.; Morelli, C.; Taddei, M.
Tetrahedron Lett. 2005, 46, 2817. (g) Desai, B.; Danks, T.
N.; Wagner, G. Tetrahedron Lett. 2005, 46, 955.
Sulfonamide 7 (0.306 g, 1 mmol) was dissolved into 2 mL of dry
THF and to this solution Cs CO (1.025 g, 3.25 mmol) was added
2
3
followed by PS-thiophenol (0.56 g of a resin with 2 mmol/g of
loading, 1.12 mmol) treated as reported above. The vial was sealed
and inserted in the cavity of a Discover system (from CEM). The
mixture was irradiated for 3 cycles of 1 min at 80 °C and 250 psi in-
ternal pressure. After cooling, the vial was opened, additional resin
was added (0.56 g), the vial was closed and then submitted to 3 ad-
ditional cycles of 1 min each at 80 °C and 250 psi internal pressure.
After cooling, the vial was opened, the contents were filtered, and
the solid was washed with THF and CH Cl . The solvent was col-
2
2
lected and evaporated to give compound 8 in 95% yield (0.114 g).
(h) Heriksen, H. S.; Cotes Oyaga, S.; Sherrington, D. C.;
Gibson, C. L. Synlett 2005, 1235.
(4) (a) Dondoni, A.; Marra, A.; Massi, A. Angew. Chem. Int. Ed.
The identity and the purity of all the amines described in Figure 1
1
were determined by comparison of their H NMR and MS spectra
2005, 44, 1672. (b) Chari, M. A.; Syamasundar, K.
with authentic samples.
Synthesis 2005, 708. (c) Baxendale, I. R.; Ernst, M.;
Krahnert, W.-R.; Ley, S. V. Synlett 2002, 1641. (d) Hon,
Y.-S.; Lee, C.-F.; Chen, R.-J.; Szu, P.-H. Tetrahedron 2001,
Acknowledgment
57, 5991. (e) Sheppeck, J. E.; Kar, H.; Hong, H. Tetrahedron
This work was financially supported by GlaxoSmithKline, Psychia-
try Centre of Excellence for Drug Discovery (Verona).
Lett. 2000, 41, 5329.
(
(
5) Green, T. W.; Wuts, P. G. M. Protective Groups in Organic
Synthesis, 3rd ed.; J. Wiley and Sons: New York, 1999, 610.
6) (a) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett.
References
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7
(
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10) Commercially available from Novabiochem. See also:
(
(
(
2
Parrott, I.; Wermuth, C.-W.; Hibert, M. Tetrahedron Lett.
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Synlett 2005, No. 19, 2996–2998 © Thieme Stuttgart · New York