Paper
Organic & Biomolecular Chemistry
448.4 mg, 0.398 mL), and NaH (60% dispersion in mineral oil,
2 equiv., 2 mmol, 83.0 mg). The mixture was stirred for 15 min
before removing from the cooling bath and warming to room
temperature. 1-Phenyl-2-(pyridin-2-yl)ethanone (1a, 1 equiv.,
1 mmol, 197.1 mg) was added and the reaction mixture was
heated to reflux for 20 hours. The reaction was then treated
with Et2O (5 mL), concentrated under reduced pressure to a
residue that was purified by flash column chromatography
(1 : 1 EtOAc–petroleum ether 40–60°) to afford the title com-
pound (203.5 mg, 92% yield).
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Acknowledgements
We thank the EPSRC National Mass Spectrometry Service
Centre, Swansea University, and Dr David Watson, Dr Gavin
Blackburn, and Tong Zhang at the Strathclyde Institute of
Pharmacy and Biomedical Sciences for analyses. We are grate-
ful to GlaxoSmithKline for the kind donation of consumables
and equipment. Dr Simon MacDonald (GSK), Dr Craig Jamie-
son (University of Strathclyde), and Pat Keating (University of
Strathclyde) are thanked for helpful discussions.
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3340 | Org. Biomol. Chem., 2013, 11, 3337–3340
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