An improved method for the palladium cross-coupling reaction of oxazol-2-ylzinc derivatives with aryl bromides

Organic Process Research and Development

Volumn 7, Issue 5, 2003, Pages 696-699

  Reeder, Michael R ^a   Gleaves, Harold E ^a   Hoover, Sheree A ^a   Imbordino, Rick J ^a   Pangborn, Jeffrey J ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; HALIDE; PALLADIUM; THIAZOLE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SCALE UP; SOLID; TECHNIQUE;

EID: 0141890129     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034059c     Document Type: Article

References (13)

1. Anderson, B. A.; Harn, N. K. Synthesis 1996, 583 and references therein.
2. (a) Hilf, C.; Bosold, F.; Harms, K.; Marsch, M.; Boche, G. Chem. Ber./Recl. 1997, 130(9), 1213.
3. (b) Vedejs, E.; Monahan, S. D. J. Org. Chem. 1996, 61, 5192.
4. (c) Hodges, J. C.; Patt, W. C.; Connolly, C. J. J. Org. Chem. 1991, 56, 449.
5. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Perdini, P. Synthesis 1987, 693.
6. 2O.
7. The n-BuLi should be added at such a rate to maintain an internal temperature below -55°C.
8. Both small- and large-scale experiments have been carried out using THF (E&M brand) directly from the bottle.
9. Residual inorganic content was determined by ROI and TGA analysis.
10. Filtration of these salts was found to be difficult for large-scale (> 100 g) coupling.
11. Fantucci, M.; Santangelo, F. WO9831687, 1997.
12. Caution: Upon warming to room temperature, butane is rapidly evolved, and care should be taken not to warm the contents too quickly. Because butane is flammable, all necessary safety precautions should be observed.
13. Residual solids can easily be filtered at this point to provide homogeneous layers.