Conjugate addition of sodium methanesulfinate to vinyl pyridines and diazines for the synthesis of aliphatic sulfones

Tetrahedron Letters

Volumn 50, Issue 17, 2009, Pages 1928-1933

  Schaaf, Gregory M ^a   Mukherjee, Sabuj ^a   Waterson, Alex G ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Conjugate addition; Medicinal chemistry; Sodium methanesulfonate; Sulfone

Indexed keywords

ACETIC ACID; MESYLIC ACID; PYRIDINE DERIVATIVE; SULFADIAZINE; SULFONE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATE; ONE POT SYNTHESIS; PURIFICATION; TEMPERATURE MEASUREMENT;

EID: 61749095948     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.037     Document Type: Article

References (16)

1. Morgenthaler M., Schweizer E., Hoffmann-Röder A., Benini F., Martin R.E., Jaeschke G., Wagner B., Fischer H., Bendels S., Zimmerli D., Schneider J., Diederich F., Kansy M., and Müller K. Chem. Med. Chem. 2 (2007) 1100-1115
2. Huang Z., Schneider C., and Benner S.A. Methods in Molecular Biology Vol. 20 (1993), Humana Press, Totowa, NJ Chapter 15
3. Parani G.A., and LaVoie E.J. Chem. Rev. 96 (1996) 3147-3176
4. Napier C., Stewart M., Melrose H., Hopkins B., McHarg A., and Wallis R. Eur. J. Pharmacol. 375 (1999) 61-74
5. Petrov K.G., Zhang Y., Carter M., Cockerill G.S., Dickerson S., Gauthier C.A., Guo Y., Mook R.A., Rusnak D.W., Walker A.L., Wood E.R., and Lackey K.E. Bioorg. Med. Chem. Lett. 16 (2006) 4686-4691
6. Farbenind, I.G. DE 623883; 1934; FTFVA6; Fortschr. Teerfarbenfabr. Verw. Industriezweige; DE; Ger.; 22; 1040.
7. Rumthao S., Lee O., Sheng S., Fu W., Mulhern D.C., Mesecar A.D., and Johnson M.E. Bioorg. Med. Chem. Lett. 14 (2004) 5165-5170
8. Chang Y., Ares J., Anderson K., Sabol B., Wallace R.A., Faroqui T., Uretsky N., and Miller D.D. J. Med. Chem. 30 (1986) 214-218
9. Dorogov M.V., Filimonov S.I., Kobylinsky D.B., Ivanovsky S.A., Korikov P.V., Soloviev M.Y., Khahina M.Y., Shalygina E.E., Kravchenko D.V., and Ivachtchenko A.V. Synthesis 18 (2004) 2999-3004
10. 6) δ ppm 9.00 (d, J = 1.83 Hz, 1H), 8.22 (dd, J = 8.15, 2.29 Hz, 1H), 7.54 (d, J = 8.06 Hz, 1H), 3.86 (s, 3H), 3.52-3.62 (m, 2H), 3.21-3.29 (m, 2H), 3.00 (s, 3 H).
11. Gipstein E., Willson C.G., and Sachdev H.S. J. Org. Chem. 45 (1980) 1486-1489
12. Molander G.A., and Rivero M.R. Org. Lett. 4 (2002) 107-109
13. a's or incomplete knowledge of the system.
14. Boyer S.J. Curr. Top. Med. Chem. 2 (2002) 973
15. 3 in MeOH. In some instances it was necessary to perform an aqueous extraction of the product after column chromatography to remove TEA salts.
16. Ten equivalents of TFA or HOAc was added due to the additional 2 equiv of TEA used during the Suzuki reaction.