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77952399191
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7
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77952363177
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Note for guidance on specification limits for residues of metal catalysts, 2002. The European Agency for the Evaluation of Medicinal Products Web site. (accessed April 21, 2010)
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Note for guidance on specification limits for residues of metal catalysts, 2002. The European Agency for the Evaluation of Medicinal Products Web site. http://www.emea.europa.eu/pdfs/human/swp/444600en.pdf (accessed April 21, 2010).
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8
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77952385282
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See, for instance
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See, for instance
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9
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77952355231
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Prasad, K.; Repic, O.; Blacklock, T. J. Org. Process Res. Dev. 2003, 7, 733-742
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Prasad, K.1
Repic, O.2
Blacklock, T.J.3
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10
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58149171584
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Pink, C. J.; Wong, H. t.; Ferreira, F. C.; Livingston, A. G. Org. Process Res. Dev. 2008, 12, 589-595
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Pink, C.J.1
Wong, H.T.2
Ferreira, F.C.3
Livingston, A.G.4
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14
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77952376167
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note
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Deprotection of 2-aminated aryloxazolines requires acidic conditions (3 M HCl, 12-24 h, reflux) which are not compatible with delicate structures. Yields do not exceed 70%, and in many instances the deprotection only leads to degradation products. See
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16
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77952378657
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note
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The reaction of 2-fluorobenzoic acid with s -BuLi and t -BuLi affords the the ipso -attack product arising out of substitution of the fluorine atom by the alkyl group
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17
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0141741402
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Gohier, F.; Castanet, A.-S.; Mortier, J. Org. Lett. 2003, 5, 1919-1922
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Gohier, F.1
Castanet, A.-S.2
Mortier, J.3
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18
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33644752654
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Metalation reactions, recent references:
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Metalation reactions, recent references: Nguyen, T. H.; Castanet, A.-S.; Mortier, J. Org. Lett. 2006, 8, 765-768
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Nguyen, T.H.1
Castanet, A.-S.2
Mortier, J.3
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19
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34247636039
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Nguyen, T. H.; Chau, N. T. T.; Castanet, A.-S.; Nguyen, K. P. P.; Mortier, J. J. Org. Chem. 2007, 72, 3419-3429
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Nguyen, T.H.1
Chau, N.T.T.2
Castanet, A.-S.3
Nguyen, K.P.P.4
Mortier, J.5
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20
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73949100605
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Tilly, D.1
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Zhao, B.-P.3
Alessi, M.4
Castanet, A.-S.5
Snieckus, V.6
Mortier, J.7
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21
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77952379131
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note
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Two recent papers described LiHMDS-promoted coupling of primary and N -substituted anilines with 2-fluorobenzoic acid (or amide) to give N -arylanthranilic acids and N -arylanthranilamides
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22
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0036181665
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Chen, M. H.; Beylin, V. G.; Iakovleva, E.; Kesten, S. J.; Magano, J.; Vrieze, D. Synth. Commun. 2002, 32, 411-417
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Chen, M.H.1
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Vrieze, D.6
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23
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28944432317
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Davis, E. M.; Nanninga, T. N.; Tjiong, H. I.; Winkle, D. D. Org. Process Res. Dev. 2005, 9, 843-846
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Davis, E.M.1
Nanninga, T.N.2
Tjiong, H.I.3
Winkle, D.D.4
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24
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77952341947
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note
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x...). See
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25
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0342473735
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A. C. Knipe, W. E. W., Ed.; John Wiley & Sons: UK
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Crampton, M. R. Organic Reaction Mechanisms; A. C. Knipe, W. E. W., Ed.; John Wiley & Sons: UK, 2004; p 189.
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Organic Reaction Mechanisms
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Crampton, M.R.1
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26
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77952389152
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note
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Lithium arylamides have weaker nucleophilic strengths than lithium dialkylamines but are more stable at higher temperature (50-60 °C).
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27
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77952394137
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note
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2 has been reported
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28
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61349134773
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Yoshida, H.; Morishita, T.; Ohshita, J. Org. Lett. 2008, 10, 3845-3847
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Yoshida, H.1
Morishita, T.2
Ohshita, J.3
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30
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77952339549
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note
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2 gave only a slight decrease of yield of the substitution product 3.
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31
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77952331704
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note
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+ forms a strong complex with the fluoro/methoxy group and the carboxylate. For the complex-induced proximity effect, CIPE, see
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32
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3242659209
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Whisler, M. N.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225
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(2004)
Angew. Chem., Int. Ed.
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Whisler, M.N.1
MacNeil, S.2
Snieckus, V.3
Beak, P.4
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33
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77952345327
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note
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2 group enters from the side almost perpendicular to the aromatic ring (to the π cloud). This is consistent with the lack of steric inhibition to addition by large groups.
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34
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77952357644
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note
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The base and TMSCl were premixed prior to addition of the acid. The deprotonation which produces a small concentration of the trappable aryllithium 18 is sufficiently rapid to make the process competitive with reaction of the hindered base with the in situ electrophile (TMSCl). See ref 11b.
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35
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77952330268
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Structure of 13 was confirmed by NOESY and HMBC (see Supporting Information)
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Structure of 13 was confirmed by NOESY and HMBC (see Supporting Information).
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36
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77952395775
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note
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2 (M = Li, K) group is a good director of ortho -metalation
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37
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15044347053
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Tilly, D.; Samanta, S. S.; De, A.; Castanet, A.-S.; Mortier, J. Org. Lett. 2005, 7, 827-830
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Tilly, D.1
Samanta, S.S.2
De, A.3
Castanet, A.-S.4
Mortier, J.5
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39
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77952364836
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Wiley-Interscience: New York
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Rappoport, Z. The Chemistry of Peroxides; Wiley-Interscience: New York, 2006; Vol. 2, part 1.
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(2006)
The Chemistry of Peroxides
, vol.2
, Issue.PART 1
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Rappoport, Z.1
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41
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77952381142
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Observations of a similar rearrangement, leading to dioxindoles, have been reported
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Observations of a similar rearrangement, leading to dioxindoles, have been reported
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42
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0035929447
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Kafka, S.; Klasek, A.; Kosmrlj, J. J. Org. Chem. 2001, 66, 6394-6399
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J. Org. Chem.
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Kafka, S.1
Klasek, A.2
Kosmrlj, J.3
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43
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77952332179
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note
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In deoxygenated medium, the reaction of 2 with LiNMeBn (5 equiv) led to 5 (> 90%). It is assumed that the reduction step leading to 25 is the first irreversible step in the pathway.
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44
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77952348257
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All new compounds gave correct analytical data. See Supporting Information
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All new compounds gave correct analytical data. See Supporting Information.
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48
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77952406666
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A patent application was filed
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A patent application was filed
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