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1
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77955169785
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Patent WO 2007/071936 A1
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Cailleau, N.; Davies, D. T.; Hennessy, A. J.; Jones, G. E.; Miles, T. J.; Pearson, N. D. Patent WO 2007/071936 A1.
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Cailleau, N.1
Davies, D.T.2
Hennessy, A.J.3
Jones, G.E.4
Miles, T.J.5
Pearson, N.D.6
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3
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77955143226
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For related quinoline metalation strategies, see
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For related quinoline metalation strategies, see
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4
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1842502953
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Bannacef, I.; Tymciu, S.; Dhilly, M.; Mongin, F.; Quéguiner, G.; Lasne, M.; Barré, L.; Perrio, C. J. Org. Chem. 2004, 69, 2622
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(2004)
J. Org. Chem.
, vol.69
, pp. 2622
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-
Bannacef, I.1
Tymciu, S.2
Dhilly, M.3
Mongin, F.4
Quéguiner, G.5
Lasne, M.6
Barré, L.7
Perrio, C.8
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8
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77955141423
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2-Chloro-5-fluoro-3-pyridinamine: $2295/kg from Archimica
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2-Chloro-5-fluoro-3-pyridinamine: $2295/kg from Archimica.
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9
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77955158445
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For a similar strategy to a [1.5]naphthyridinone, see
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For a similar strategy to a [1.5]naphthyridinone, see
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-
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10
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85008112619
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Sakamoto, T.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1985, 33, 4764
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(1985)
Chem. Pharm. Bull.
, vol.33
, pp. 4764
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-
Sakamoto, T.1
Kondo, Y.2
Yamanaka, H.3
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11
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0035036499
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Li, J.; Zheng, L.; King, I.; Doyle, T. W.; Chen, S. Curr. Med. Chem. 2001, 8, 121
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(2001)
Curr. Med. Chem.
, vol.8
, pp. 121
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Li, J.1
Zheng, L.2
King, I.3
Doyle, T.W.4
Chen, S.5
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12
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85027892580
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-
references cited therein
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Littke, A. F.; Fu, G. C. Org. Synth. 2005, 81, 63 and references cited therein
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(2005)
Org. Synth.
, vol.81
, pp. 63
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Littke, A.F.1
Fu, G.C.2
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15
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0032747809
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Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550
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(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 9550
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-
Wolfe, J.P.1
Singer, R.A.2
Yang, B.H.3
Buchwald, S.L.4
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16
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77955146253
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A similar path to a [1,8]naphthyridinone has been reported in 42% yield
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A similar path to a [1,8]naphthyridinone has been reported in 42% yield
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17
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0028012087
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Singh, B.; Bacon, E. R.; Robinson, S.; Fritz, R. K.; Lesher, G. Y.; Kumar, V.; Dority, J. A.; Reuman, M.; Kuo, G.; Eissenstat, M. A.; Pagani, E. D.; Bode, D. C.; Bentley, R. G.; Connell, M. J.; Hamel, L. T.; Silver, P. J. J. Med. Chem. 1994, 37, 248
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(1994)
J. Med. Chem.
, vol.37
, pp. 248
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Singh, B.1
Bacon, E.R.2
Robinson, S.3
Fritz, R.K.4
Lesher, G.Y.5
Kumar, V.6
Dority, J.A.7
Reuman, M.8
Kuo, G.9
Eissenstat, M.A.10
Pagani, E.D.11
Bode, D.C.12
Bentley, R.G.13
Connell, M.J.14
Hamel, L.T.15
Silver, P.J.16
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18
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77955136757
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2NMe and xylene at 135 °C, the reaction from isolated 9 to napthyridinone 7 was very slow, suggesting that Pd catalyst is needed for the conversion
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2NMe and xylene at 135 °C, the reaction from isolated 9 to napthyridinone 7 was very slow, suggesting that Pd catalyst is needed for the conversion.
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19
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77955143225
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2 reaction in order to alleviate safety concerns around the potential formation of dimethylcarbamoyl chloride (DMCC), a known potent carcinogen. See
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2 reaction in order to alleviate safety concerns around the potential formation of dimethylcarbamoyl chloride (DMCC), a known potent carcinogen. See
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21
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77955168606
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The mono-HCl salt of 10 did not react with MeOH; however, even a catalytic amount of HCl could convert the mono-HCl salt to 11. Thanks to Huan Wang (GSK) for this suggestion
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The mono-HCl salt of 10 did not react with MeOH; however, even a catalytic amount of HCl could convert the mono-HCl salt to 11. Thanks to Huan Wang (GSK) for this suggestion.
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22
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77955160175
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For a review, see
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For a review, see
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23
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34250771010
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Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 47, 3802
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(2007)
Angew. Chem., Int. Ed.
, vol.47
, pp. 3802
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Mulvey, R.E.1
Mongin, F.2
Uchiyama, M.3
Kondo, Y.4
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24
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77955168535
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This regiochemical discrepancy has been observed in deprotonation of pyridines
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This regiochemical discrepancy has been observed in deprotonation of pyridines
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-
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25
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0035824331
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The regiochemistry of the undesired mono-iodide has not been confirmed
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Imahori, T.; Uchiyama, M.; Sakamoto, T.; Kondo, Y. Chem. Commun. 2001, 2450 The regiochemistry of the undesired mono-iodide has not been confirmed.
-
(2001)
Chem. Commun.
, pp. 2450
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Imahori, T.1
Uchiyama, M.2
Sakamoto, T.3
Kondo, Y.4
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26
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77955155998
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2Li is known to react with haloarenes to form benzynes
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2Li is known to react with haloarenes to form benzynes
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27
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0037167004
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Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sadamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514
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(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 8514
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Uchiyama, M.1
Miyoshi, T.2
Kajihara, Y.3
Sadamoto, T.4
Otani, Y.5
Ohwada, T.6
Kondo, Y.7
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28
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77955149809
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A report of the unsuccessful use of this reagent in a screen of various zincate bases has appeared
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A report of the unsuccessful use of this reagent in a screen of various zincate bases has appeared
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29
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22244485005
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Gauthier, D. R., Jr.; Limanto, J.; Devine, P. N.; Desmond, R. A.; Szumigala, R. H., Jr.; Foster, B. S.; Volante, R. P. J. Org. Chem. 2005, 70, 5938
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(2005)
J. Org. Chem.
, vol.70
, pp. 5938
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Gauthier Jr., D.R.1
Limanto, J.2
Devine, P.N.3
Desmond, R.A.4
Szumigala Jr., R.H.5
Foster, B.S.6
Volante, R.P.7
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30
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19844379032
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Marzi, E.; Bobbio, C.; Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2005, 2116
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(2005)
Eur. J. Org. Chem.
, pp. 2116
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Marzi, E.1
Bobbio, C.2
Cottet, F.3
Schlosser, M.4
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32
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22944470788
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Pei, W.; Mo, J.; Xiao, J. J. Organomet. Chem. 2005, 690, 3546
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(2005)
J. Organomet. Chem.
, vol.690
, pp. 3546
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Pei, W.1
Mo, J.2
Xiao, J.3
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33
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77955148690
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A 65-70% yield was obtained via EtOAc/cyclohexane crystallization; however, this procedure remains in need of optimization
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A 65-70% yield was obtained via EtOAc/cyclohexane crystallization; however, this procedure remains in need of optimization.
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-
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34
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77955123896
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Chloromethane is generated in the conversion of 17 to 18 and safety precautions (proper ventilation) were taken
-
Chloromethane is generated in the conversion of 17 to 18 and safety precautions (proper ventilation) were taken.
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-
35
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77955124140
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With the opposite enantiomers of 16, 17, and 18, an overall yield of 71% was obtained when epoxy alcohol 17 was isolated
-
With the opposite enantiomers of 16, 17, and 18, an overall yield of 71% was obtained when epoxy alcohol 17 was isolated.
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-
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-
36
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0030583489
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Klar, U.; Neef, G.; Vorbruggen, H. Tetrahedron Lett. 1996, 37, 7497
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 7497
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Klar, U.1
Neef, G.2
Vorbruggen, H.3
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