| Autor: |
Ragan, J. A., Raggon, J. W., Hill, P. D., Jones, B. P., McDermott, R. E., Munchhof, M. J., Marx, M. A., Casavant, J. M., Cooper, B. A., Doty, J. L., Lu, Y. |
| Zdroj: |
Organic Process Research & Development; September 2003, Vol. 7 Issue: 5 p676-683, 8p |
| Abstrakt: |
The multihundred-gram synthesis of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl]-(2-methyl-1H-indol-5-yl)-amine (1) is described utilizing a Stille cross-coupling of an iodothienopyridine (3) with 5-(tributylstannyl)-1-methylimidazole (11). Several cross-coupling methods were evaluated for the conversion of thienopyridine 3 to imidazole−thienopyridine 2, but only two were effective: the Stille coupling and a Negishi cross-coupling of the organozinc reagent derived from 2-(tert-butyldimethylsilyl)-1-methylimidazole and iodothienopyridine (3). The latter procedure worked well on laboratory scale (<50 g), but was capricious upon scale-up. The issues with scale-up of an organostannane reagent are discussed, including control and analysis of organotin levels. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
|
