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Synthesis 2021; 53(05): 961-970
DOI: 10.1055/a-1339-3227
DOI: 10.1055/a-1339-3227
paper
Late-Stage Transformation of Carboxylic Acids to N-Trifluoroethylimides with Trifluoromethyl Diazomethane
We thank the Outstanding Young Talents Funding of Jiangxi Province (20171BCB23039) for funding this research.
Abstract
We report the first systematic evaluation of the reaction of trifluoromethyl diazomethane (2,2,2-trifluorodiazoethane, CF3CHN2) with drug-like molecules. We found our previous copper-catalyzed transformation of carboxylic acids to the corresponding N-trifluoroethylimides with CF3CHN2 and acetonitrile is well-suited for the late-stage modification of drug and drug-like acids. A procedure that enables the use of solid nitriles and nitriles with high boiling points as viable substrates is also disclosed.
Key words
N-trifluoroethylimides - trifluoromethyl diazomethane - late-stage functionalization - fluoroalkyl - copper - trifluoromethyl - 2,2,2-trifluorodiazoethaneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1339-3227.
- Supporting Information
Publication History
Received: 15 October 2020
Accepted after revision: 17 December 2020
Accepted Manuscript online:
17 December 2020
Article published online:
18 January 2021
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