A Novel and Efficient Continuous-Flow Route To Prepare Trifluoromethylated N-Fused Heterocycles for Drug Discovery and Pharmaceutical Manufacturing | Zendy

Lara Amini-Rentsch | Zendy; Ennio Vanoli | Zendy; Sylvia RichardBildstein | Zendy; Roger Martí | Zendy; Gianvito Vilé | Zendy

Open Access

A Novel and Efficient Continuous-Flow Route To Prepare Trifluoromethylated N-Fused Heterocycles for Drug Discovery and Pharmaceutical Manufacturing

Author(s) -

Lara Amini-Rentsch,

Ennio Vanoli,

Sylvia RichardBildstein,

Roger Martí,

Gianvito Vilé

Publication year - 2019

Publication title -

industrial and engineering chemistry research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.878

H-Index - 221

eISSN - 1520-5045

pISSN - 0888-5885

DOI - 10.1021/acs.iecr.9b01906

Subject(s) - continuous flow , yield (engineering) , flow chemistry , combinatorial chemistry , trifluoroacetic anhydride , trifluoromethyl , trifluoroacetic acid , scalability , chemistry , alkylation , pharmaceutical manufacturing , computer science , functional group , drug discovery , biochemical engineering , organic chemistry , process engineering , catalysis , materials science , engineering , bioinformatics , biochemistry , alkyl , polymer , database , metallurgy , biology

Continuous-flow processing has become one of the fastest-growing research areas in chemistry in the last 10 years. Herein we disclose an automated and scalable continuous-flow route for the quick introduction of trifluoromethyl groups on a variety of heterocycles, with application in drug discovery and manufacturing. This involves the direct alkylation-cyclization of amines in the presence of trifluoroacetic acid or anhydride, cheap and readily available CF3-containing building blocks. Compared to traditional batch reactions involving an intermediate purification step, the continuous-flow reactions occurred quickly and at mild conditions, with high yield and broad functional-group tolerance. The practical utility of the method was demonstrated by a gram-scale synthesis and by the estimation of modern green metrics.

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