7
ACCEPTED MANUSCRIPT
5. Ratheesh, M.; Sindhu, G.; Helen, A. Inflammation Res. 2013,
brine, dried over Na2SO4, filtered and concentrated under
reduced pressure. The crude product was purified by column
chromatography (PE:EA = 100:1) to afford the title compound
(335 mg, 79% yield) as a white solid.
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4.3.26. 6-Chloro-2-phenylquinoline (21): To a 10 mL two
necked flask was added 11b (50 mg, 0.21 mmol),
phenylboronic acid (28 mg, 0.23 mmol), potassium fluoride
(36 mg, 0.62 mmol) and Pd2(dba)3 (9.5 mg, 0.01 mmol) in this
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t
(0.08 ml) and Bu3P solution (0.12 ml, 0.04 mmol, 10% in
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hexane). The whole system was then heated to 85 ꢀ under the
protection of argon. The reaction was complete in three hours
indicated by HPLC. After cooling down to r.t., 2 ml of EA and
1 ml of water were added to the mixture and kept stirring for
fifteen minutes. The resulting mixture was filtered and the
filter cake was washed with EA. The mother liquor was then
separated and the aqueous phase was extracted with EA. The
combined organic solution was dried over anhydrous Na2SO4,
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was purified by column chromatography (PE:EA = 50:1) to
afford the titled compound 21 (45 mg, 90%) as a white solid.
The spectroscopic data are consistent with previously
reported.26d 1H NMR (400 MHz, CDCl3) δ 8.15 (d, J = 7.2 Hz,
2H), 8.09 (dd, J = 8.7, 5.9 Hz, 2H), 7.87 (d, J = 8.7 Hz, 1H),
7.78 (d, J = 2.2 Hz, 1H), 7.65 (dd, J = 9.0, 2.2 Hz, 1H), 7.53 (t,
J = 7.3 Hz, 2H), 7.49 (d, J = 7.0 Hz, 1H); 13C NMR (100 MHz,
CDCl3) δ 157.6, 146.8, 139.3, 135.9, 132.0, 131.4, 130.6,
129.7, 129.0, 127.8, 127.6, 126.2, 119.8.
9.
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Acknowledgements
Financial support from Tianjin Natural Science Foundation
of China (15JCYBJC53400) and International Science
&
Technol-ogy Cooperation Program of China (2013DFA31160)
are greatly acknowledged. The authors are thankful to the
Research Center of Modern Analytical Technology, Tianjin
University of Science and Technology for NMR
measurements and high resolution mass analysis.
Supplenmentary Data
Supplementary data (Supplementary data associated with
this article, including materials and methods and NMR spectra)
associated with this article can be found in the online version
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References and notes
1. Lam, K.-H.; Lee, K. K.-H.; Gambari, R.; Kok, S. H.-L.; Kok,
T.-W.; Chan, A. S.-C.; Bian, Z.-X.; Wong, W.-Y.; Wong, R.
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19. The bromination of quinoline N-oxide with POBr3 in DCM was
reported in this paper: Gopinath, V. S.; Pinjari, J.; Dere, R. T.;
Verma, A.; Vishwakarma, P.; Shivahare, R.; Moger, M.;
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20. This can be explained by the reasonance forms. As can be seen
from the following reasonance forms, there are three stable
reasonance forms (8, 8’ and 8’’) for quinoline N-oxides,
whereas only two stable reasonace forms (13a and 13a’) exist
for isoquinoline N-oxides. 13a’’ is unstable due to destroying
benzene ring aromaticity.
4. Vandekerckhove, S.; Tran, H. G.; Desmet, T.; D'Hooghe, M.
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