Formation of tetra-substituted enamides and stereoselective...

Details Formation of tetra-substituted enamides and stereoselective... Formation of tetra-substituted enamides and stereoselective...

C - Chemistry, Metallurgy

07

C

C07C 233/00 (2006.01) C07D 211/72 (2006.01)

Patent

CA 2572845

The present invention is directed to a practical process for the preparation of an enamide (II) by palladium catalyzed coupling of a primary amide (IV) with a compound of structural formula (III), as shown below: As well as to crystalline forms of a compound produced by this process, in particular, an anhydrous crystal form, Form B, and crystalline solvates falling into three patterns, Type 1, Type 2, and Type 3, and crystalline intermediate compounds produced in the process. Still further, the present invention relates to the stereoselective reduction of the tetrasubstituted enamide (II) to the corresponding amide (I).

La présente invention concerne un procédé pratique de préparation d'un énamide (II) par couplage catalysé par le palladium d'un amide primaire (IV) avec un composé de formule structurale (III). L'invention concerne également des formes cristallines d'un composé produit selon ledit procédé, en particulier, une forme cristalline anhydre, forme B, ainsi que des solvates cristallins correspondant à trois modèles, type 1, type 2 et type 3 et des composés intermédiaires cristallins produits lors de la mise en oeuvre du procédé. La présente invention concerne enfin la réduction stéréosélective de l'énamide tétrasubstitué (II) en amide correspondant (I).

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