… Methods for the Large-Scale Preparation of an Imidazole-Thienopyridine: Synthesis of [2-(3-Methyl-3H-imidazol-4-yl)-thieno [3, 2-b] pyridin-7-yl]-(2-methyl-1H-indol-5- …

…, BP Jones, RE McDermott, MJ Munchhof…

Index: Ragan; Raggon; Hill; Jones; McDermott; Munchhof; Marx; Casavant; Cooper; Doty; Lu Organic Process Research and Development, 2003 , vol. 7, # 5 p. 676 - 683

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Citation Number: 37

Abstract

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- ...