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Volumn 14, Issue 1, 2010, Pages 263-271

Optimisation of permanganate oxidation and suzuki-miyaura coupling steps in the synthesis of a Nav1.8 Sodium channel modulator

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EID: 77149130182     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900092h     Document Type: Article
Times cited : (22)

References (47)
  • 10
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    • WO 98/38174, also commercially available from Alfa Aesar, Heysham, Lancashire, U.K., cat. no. L17511, CAS 212779-19-6
    • Cox, B.; Nobbs, M. S.; Shah, G. P.; Edney, D. D.; Loft, M. S. PCT Int. Appl. WO 98/38174, 1998, CAN 129:230741, AN 1998:608606; also commercially available from Alfa Aesar, Heysham, Lancashire, U.K., cat. no. L17511, CAS 212779-19-6.
    • (1998) PCT Int. Appl.
    • Cox, B.1    Nobbs, M.S.2    Shah, G.P.3    Edney, D.D.4    Loft, M.S.5
  • 11
    • 0005861625 scopus 로고
    • CAS registry 126325-46-0. We purchased from Asymchem, Morrisville, NC, U.S.A
    • Dunn, A. D.; Currie, A.; Hayes, L. E. J. Prakt. Chem. (Leipzig) 1989, 331, 369. CAS registry 126325-46-0. We purchased from Asymchem, Morrisville, NC, U.S.A.
    • (1989) J. Prakt. Chem. (Leipzig) , vol.331 , pp. 369
    • Dunn, A.D.1    Currie, A.2    Hayes, L.E.3
  • 13
    • 37049109963 scopus 로고
    • Pyridine has been used as solvent in conjunction with permanganate. See
    • Pyridine has been used as solvent in conjunction with permanganate. See: Sala, T.; Sargent, M. V. J. Chem. Soc. Chem. Commun. 1978, 253
    • (1978) J. Chem. Soc. Chem. Commun. , pp. 253
    • Sala, T.1    Sargent, M.V.2
  • 16
    • 0034693279 scopus 로고    scopus 로고
    • for the des-bromo case, but interestingly they isolated the acetate salt, not the free base
    • Compare Zafar, A.; Geib, S. J.; Hamuro, Y.; Carr, A. J.; Hamilton, A. D. Tetrahedron 2000, 56, 8419. ; for the des-bromo case, but interestingly they isolated the acetate salt, not the free base.
    • (2000) Tetrahedron , vol.56 , pp. 8419
    • Zafar, A.1    Geib, S.J.2    Hamuro, Y.3    Carr, A.J.4    Hamilton, A.D.5
  • 17
    • 77149171333 scopus 로고    scopus 로고
    • 5-Bromo-4-chloro-3-methoxypyridine-2-carboxylic acid readily de- carboxylates at only 120 °C
    • 5-Bromo-4-chloro-3-methoxypyridine-2-carboxylic acid readily de- carboxylates at only 120 °C
  • 21
    • 0034804379 scopus 로고    scopus 로고
    • Addition of phosphate to the permanganate oxidation of aldehydes has been found to be beneficial, see
    • Addition of phosphate to the permanganate oxidation of aldehydes has been found to be beneficial, see: Takemoto, T.; Yasuda, K.; Ley, S. V. Synlett 2001, 1555.
    • (2001) SynLett. , pp. 1555
    • Takemoto, T.1    Yasuda, K.2    Ley, S.V.3
  • 30
    • 77149137880 scopus 로고    scopus 로고
    • More recently the search for alternatives to phosphine ligands has provided a number of catalyst systems capable of achieving biaryl cross-couplings in good yield
    • More recently the search for alternatives to phosphine ligands has provided a number of catalyst systems capable of achieving biaryl cross-couplings in good yield
  • 34
    • 77149133581 scopus 로고    scopus 로고
    • 2 and gave 70-75% yield on 10-18 g scale
    • 2 and gave 70-75% yield on 10-18 g scale.
  • 35
    • 77149158651 scopus 로고    scopus 로고
    • This was important as over-reaction was observed if the temperature was allowed to rise unduly with the excess boronic acid coupling to a chloro substituent
    • This was important as over-reaction was observed if the temperature was allowed to rise unduly with the excess boronic acid coupling to a chloro substituent.


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