A convenient synthesis of heteroaryl benzoic acids via Suzuki reaction

Synlett

Volumn , Issue 6, 2000, Pages 829-831

  Gong, Yong ^a   Pauls, Henry W ^a  

^a Rhone Poulenc Rorer ^*  (United States)

Author keywords

Biaryls; Carboxylic acids; Cross coupling; Heteroaryl halides; Palladium

Indexed keywords

BENZOIC ACID DERIVATIVE; PALLADIUM; SODIUM CARBONATE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034124907     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. Negishi, E.-I. Acc. Chem. Res. 1982, 15, 340.
2. Matsushita, Y.; Sakamoto, K.; Murakami, T.; Matsui, T. Synth. Commun. 1994, 24, 3307.
3. a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
4. b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. The Stille reaction has also been widely applied in biaryl synthesis:
5. c) Stanfort, S. P. Tetrahedron 1998, 54, 263.
6. d) Genet, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305.
7. a) Johnson, M. G.; Foglesong, R. J. Tetrahedron Lett. 1997, 38, 7001.
8. b) Caron, S.; Hawkins, J. M. J. Org. Chem. 1998, 63, 2054.
9. Snieckus, V. Chem. Rev. 1990, 90, 879.
10. Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G.; Carstaris, A. Org. Proc. Res. Dev. 1999, 3, 248.
11. 2. The aqueous layer was acidified with cone. HCl and the resulting precipitate was collected and washed with water.
12. +, 100%), 182 (33%), 154 (42%).
13. Suzuki coupling of 2-and 4-chloropyridines has been reported: Lohse, O.; Thevenin, P.; Waldvogel, E. Synlett 1999, 45.
14. 2 and water.
15. b of aryl halides were well documented. a) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619.
16. b) Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C; Lemaire, M. Tetrahedron Lett. 1998, 39, 2559.
17. 2. The reaction was worked up as before.
18. For distinguishing pyrimidine regioisomers via NOE, see: Sandosham, J.; Undheim, K.; Rise, F. Heterocycles 1993, 35, 235.
19. Compounds 7b and 7e are soluble in water. Reverse phase HPLC was applied to their purification.