1790
Q.-H. Zheng et al. / Bioorg. Med. Chem. Lett. 13 (2003) 1787–1790
Winkle, W.; Vavrek, T.; Mock, B. H.; Zipes, D. P. J. Nucl.
Med. 1999, 40, 846.
15. Olgin, J. E.; Sih, H. J.; Hanish, S.; Jayachandran, J. V.;
Wu, J. S.; Zheng, Q.-H.; Winkle, W.; Mulholland, G. K.;
26. Experimental procedure: (A) General: all commercial
reagents and solvents were used without further purification.
H NMR spectra were recorded on a Bruker QE 300 NMR
1
spectrometer using tetramethylsilane (TMS) as an internal
standard. Chemical shift data for the proton resonances were
reported in parts per million (d) relative to internal standard
TMS (d 0.0). Chromatographic solvent proportions are
expressed on a volume: volume basis. Thin layer chromato-
graphy was run using Analtech silica gel GF uniplates (5Â10
Zipes, D. P.; Hutchins, G. Circulation 1998, 98, 2608.
6. Jewett, D. M. Appl. Radiat. Isot. 1992, 43, 1383.
1
1
7. Mock, B. H.; Mulholland, G. K.; Vavrek, M. T. Nucl.
Med. Biol. 1999, 26, 467.
8. Mulholland, G. K.; Zheng, Q.-H. Abstracts of Papers of
the American Chemical Society 1996, 212 76-NUCL.
1
2
cm ). Plates were visualized by UV light. Normal phase flash
1
2
2
9. Zheng, Q.-H.; Mulholland, G. K. Nucl. Med. Biol. 1996,
3, 981.
0. Fei, X. S.; Zheng, Q-H.; Hutchins, G. D.; Liu, X.; Stone,
chromatography was carried out on EM Science silica gel 60
(230–400 mesh) with a forced flow of the indicated solvent
system in the proportions described below. The reaction was
performed under a positive pressure of nitrogen maintained by
a direct line from a nitrogen source. (B) 3-(Ethylmethylami-
no)phenol (5): a mixture of 3-ethylaminophenol (4, 1.37 g, 10
mmol), potassium carbonate (2.07 g, 15 mmol), methyl iodide
K. L.; Carlson, K. A.; Mock, B. H.; Winkle, L.; Glick-Wilson,
B. E.; Miller, K. D.; Fife, R. S.; Sledge, G. W.; Sun, H. B.;
Carr, R. E. J. Labelled Compd. Radiopharm. 2002, 45, 449.
21. Zheng, Q.-H.; Fei, X. S.; Liu, X.; Wang, J.-Q.; Sun, H. B.;
Mock, B. H.; Stone, K. L.; Martinez, T. D.; Miller, K. D.;
3
(1.42 g, 10 mmol), and CH CN (50 mL) was stirred at room
Sledge, G. W.; Hutchins, G. D. Nucl. Med. Biol. 2002, 29, 761.
temperature under nitrogen overnight. The suspension was
filtered and the filtrate was taken down to dryness under
vacuum. The residue was adsorbed onto a silica gel column
and eluted with 1:6 EtOAc:hexane to give the title compound
2
2. Mulholland, G. K.; Zheng, Q.-H.; Mock, B. H.; Vavrek,
M. T. J. Labelled Compd. Radiopharm. 1999, 42 (Suppl. 1), S459.
3. Zheng, Q.-H.; Stone, K. L.; Mock, B. H.; Miller, K. D.;
2
Fei, X.; Liu, X.; Wang, J.-Q.; Glick-Wilson, B. E.; Sledge,
G. W.; Hutchins, G. D. Nucl. Med. Biol. 2002, 29, 803.
f
5 (450 mg, 29.8%) as a yellow oil, R =0.60 (1:3 EtOAc:hex-
1
ane). H NMR (300 MHz, CDCl ): d 1.05 (t, 3H, J =7.4 Hz,
3
1
2
4. Pascali, C.; Bongi, A.; Iwata, R.; Cambie, M.; Bombar-
dieri, E. J. Labelled Compd. Radiopharm. 2000, 43, 195.
5. Zheng, Q.-H.; Hutchins, G. D.; Mock, B. H. J. Labelled
Compd. Radiopharm. 2001, 44 (Suppl. 1), S410.
J
2
=6.6 Hz, NCH
2
CH
2H, J =7.4 Hz, J =6.6 Hz, NCH CH ), 5.70 (brs, 1H, OH),
3
), 2.80 (s, 3H, NCH
3
), 3.26–3.33 (dd,
1
2 2 3
2
6.17–6.19 (m, 2H, ArH), 6.30–6.32 (m, 1H, ArH), 7.02–7.07
(m, 1H, ArH).