The preparation of heterobiaryl phosphonates via the Stille coupling reaction

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7611-7614

  Kennedy, Gordon ^a   Perboni, Alcide D ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030583496     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01674-7     Document Type: Article

References (11)

1. 1. Bringmann, G., Walter, R., and Weirich, R., Ang. Chem. Int. Ed. Engl., 1990, 29, 977
2. 2. Kalinin, V.N., Synthesis, 1992, 413, Stille, J. K., Ang. Chem. Int. Ed. Engl., 1986, 25, 505; Mitchell, T.N., Synthesis, 1992, 803
3. Kalinin, V.N., Synthesis, 1992, 413, Stille, J. K., Ang. Chem. Int. Ed. Engl., 1986, 25, 505; Mitchell, T.N., Synthesis, 1992, 803
4. Kalinin, V.N., Synthesis, 1992, 413, Stille, J. K., Ang. Chem. Int. Ed. Engl., 1986, 25, 505; Mitchell, T.N., Synthesis, 1992, 803
5. 3. Yoshino, K., et al., J. Med. Chem., 1986, 29, 820
6. 4. 2-tributylstannyl-N-methylimidazole: Molloy, K.C., Waterfield, P.C., Mahon, M.F., J. Organometallic Chem., 1989, 365, 61; 2-tributylstannyl-pyridine, thiophene, thiazole: Peters, D., Homfeldt, A.-B., Gronowitz, S., J. Het. Chem., 1990, 27, 2165; 4-tributylstannyl-pyrimidine: Arukwe, J., Benneche, T., Undheim, K., J. Chem. Soc. Perkin Trans., 1989, 255
7. 2-tributylstannyl-N-methylimidazole: Molloy, K.C., Waterfield, P.C., Mahon, M.F., J. Organometallic Chem., 1989, 365, 61; 2-tributylstannyl-pyridine, thiophene, thiazole: Peters, D., Homfeldt, A.-B., Gronowitz, S., J. Het. Chem., 1990, 27, 2165; 4-tributylstannyl-pyrimidine: Arukwe, J., Benneche, T., Undheim, K., J. Chem. Soc. Perkin Trans., 1989, 255
8. 2-tributylstannyl-N-methylimidazole: Molloy, K.C., Waterfield, P.C., Mahon, M.F., J. Organometallic Chem., 1989, 365, 61; 2-tributylstannyl-pyridine, thiophene, thiazole: Peters, D., Homfeldt, A.-B., Gronowitz, S., J. Het. Chem., 1990, 27, 2165; 4-tributylstannyl-pyrimidine: Arukwe, J., Benneche, T., Undheim, K., J. Chem. Soc. Perkin Trans., 1989, 255
9. 2 was refluxed for 6.5h. The mixture was cooled, diluted with acetonitrile and washed with petroleum ether (40-70) (5 x 25ml), solvent removed and the residual oil chromatographed on silica to give 147mg (78%) diethyl-p-(2-N-methylimidazolyl)benzylphosphonate as a colourless oil. All compounds gave satisfactory spectroscopic analyses.
10. 6. Bailey, T.R., Tet. Letts., 1986, 27, 4407.
11. 7. The presence of ortho substituents in the stannane appears to be an impediment to successful reaction in the attempted couplings with highly hindered electron rich triflates: Saa, J. M., Martorell, G., Garcia-Rosa, A., J. Org. Chem., 1992, 57, 678