We report herein a synthetic protocol for the preparation of 1,3-dibromo-1,1-difluoro-2-propanone, a new synthon used for the first time in a reaction with aromatic amines and sodium thiocyanate, leading to thiazoles which are useful candidates in drug discovery programs. The new synthon allows to introduce a bromodifluoromethyl group at the C4 of the thiazole, and it is amenable of further transformation such as the Br/F exchange useful in radiopharmaceutics. Application of the strategy to the preparation of a precursor of the biologically relevant DF2755Y is also reported.

1,3-Dibromo-1,1-difluoro-2-propanone as a Useful Synthon for a Chemoselective Preparation of 4-Bromodifluoromethyl Thiazoles

Colella, Marco;MUSCI, PANTALEO;Carlucci, Claudia;Degennaro, Leonardo;Luisi, Renzo
2018

Abstract

We report herein a synthetic protocol for the preparation of 1,3-dibromo-1,1-difluoro-2-propanone, a new synthon used for the first time in a reaction with aromatic amines and sodium thiocyanate, leading to thiazoles which are useful candidates in drug discovery programs. The new synthon allows to introduce a bromodifluoromethyl group at the C4 of the thiazole, and it is amenable of further transformation such as the Br/F exchange useful in radiopharmaceutics. Application of the strategy to the preparation of a precursor of the biologically relevant DF2755Y is also reported.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11586/224701
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