P. LaBeaume et al. / Tetrahedron Letters 51 (2010) 1906–1909
1909
and charged with argon. Freshly distilled DMF (0.5 mL) was added
References and notes
followed by N,N0-dimethyl ethylenediamine (0.0265 g, 0.30 mmol).
The vial was capped with a CEM Corp. PL cap (SP1318A) and stirred
in the cavity of a CEM DiscoverÒ Lab Mate reactor at 110 °C
for 17 min (200 W, 300 psi). The residue was purified by silica gel
column chromatography (9:1 hexanes/ethyl acetate) and concen-
trated in vacuo to yield the title compound (0.0330 g, 88%) as a
yellow oil.
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2.2. 4-Fluoro-2-pyridinecarbonitrile
4-Nitro-2-pyridinecarbonitrile (0.0298 g, 0.2 mmol) was added
to a flame-dried 14 ꢂ 86 mm (OD) glass microwave tube and
charged with argon. Anhydrous TBAF (0.5 mL of a 1 M solution in
DMSO, 0.5 mmol) was then added at 25 °C. The vial was capped
with a CEM Corp. PL cap (SP1318A) and stirred in the cavity of a
CEM DiscoverÒ Lab Mate reactor set at 25 °C for 2 min (300 W,
250 psi). The reaction mixture was diluted with water (5 mL), ex-
tracted with diethyl ether (2 ꢂ 5 mL), washed with brine
(1 ꢂ 5 mL), dried (MgSO4), and concentrated in vacuo. The residue
was purified by filtration through a plug of silica gel to yield the ti-
tle compound (0.024 g, 99%) as a white solid mp 72–74 °C;9 TLC
(hexanes/ethyl acetate = 4:1); 1H NMR (500 MHz, CDCl3) d 7.28–
7.33 (m, 1H), 7.47 (dd, J = 2.5, 8 Hz, 1H), 8.72 (dd, J = 5.5, 8 Hz,
1H); 13C NMR (125 MHz, CDCl3) d 115.4, 117.2, 136.2, 153.9,
167.4, 169.6.
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Acknowledgments
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We thank the Alzheimer’s Drug Discovery Foundation (ADDF)
and the Institute for the Study of Aging (ISOA) Inc. for financial
support of this work (project #281004).
16. Saito, S.; Koizumi, Y. Tetrahedron Lett. 2005, 46, 4715–4717.