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Volumn 5, Issue 17, 2003, Pages 3131-3134

Efficient synthesis of 2-aryl-6-chloronicotinamides via PXPd2-catalyzed regioselective Suzuki coupling

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DICHLORONICOTINAMIDE; AMIDE; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; METHANOL; NICOTINAMIDE DERIVATIVE; PALLADIUM; POTASSIUM CARBONATE; REAGENT; UNCLASSIFIED DRUG;

EID: 0141855350     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035188g     Document Type: Article
Times cited : (63)

References (21)
  • 3
    • 0141623987 scopus 로고    scopus 로고
    • note
    • 2Ph were irradiated.
  • 4
    • 0034533365 scopus 로고    scopus 로고
    • Hirokawa obtained a mixture of regioisomers upon addition of amines to 2,6-dichloronicotinic acid methyl ester, with the 2-amino regioisomer predominating
    • Hirokawa, Y.; Horikawa, T.; Kato, S. Chem. Pharm. Bull. 2000, 12, 1847. Hirokawa obtained a mixture of regioisomers upon addition of amines to 2,6-dichloronicotinic acid methyl ester, with the 2-amino regioisomer predominating.
    • (2000) Chem. Pharm. Bull. , vol.12 , pp. 1847
    • Hirokawa, Y.1    Horikawa, T.2    Kato, S.3
  • 5
    • 0034712156 scopus 로고    scopus 로고
    • 2 ligand can be thought of as a bidentate ligand since Buchwald proposed participation of the π-system of the ortho aromatic with the unoccupied d-orbital on palladium
    • 2 ligand can be thought of as a bidentate ligand since Buchwald proposed participation of the π-system of the ortho aromatic with the unoccupied d-orbital on palladium.
    • (2000) J. Org. Chem. , vol.65 , pp. 1158
    • Wolfe, J.P.1    Tomori, H.2    Sadighi, J.P.3    Yin, J.4    Buchwald, S.L.5
  • 6
    • 0035857404 scopus 로고    scopus 로고
    • However, Hartwig has shown that the oxidative addition can be reversible. Roy, A. H.; Hartwig, J. F. J. J. Am. Chem. Soc. 2001, 123, 1232.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1232
    • Roy, A.H.1    Hartwig, J.F.J.2
  • 7
    • 0141512742 scopus 로고    scopus 로고
    • note
    • 2 carbon-halide bonds has been proposed.
  • 15
    • 0035901659 scopus 로고    scopus 로고
    • (b) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1513
    • Li, G.Y.1
  • 17
    • 0141512741 scopus 로고    scopus 로고
    • POPd2, CAS #386706-32-7, was commercially available from CombiPhos Catalysts, Inc.
    • POPd2, CAS #386706-32-7, was commercially available from CombiPhos Catalysts, Inc. http://www.combiphos.com.
  • 18
    • 0141512740 scopus 로고    scopus 로고
    • PXPd2, CAS 386706-33-8, was available exclusively from CombiPhos Catalysts, Inc.
    • PXPd2, CAS 386706-33-8, was available exclusively from CombiPhos Catalysts, Inc. http://www.combiphos.com.
  • 19
    • 0141847333 scopus 로고    scopus 로고
    • note
    • Methanol and ethanol are preferred solvents with the Pd/phosphinous acid complexes. Li, G. Y. Personal communication.
  • 21
    • 0141623985 scopus 로고    scopus 로고
    • note
    • 3): δ 40.0, 66.0, 114.8, 119.9, 121.6, 127.9, 129.0, 129.3, 129.4, 129.8, 130.1, 130.6, 137.4, 137.8, 139.7, 156.1, 158.4, 158.5, 168.8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.