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Synthesis 2023; 55(21): 3600-3609
DOI: 10.1055/a-2116-6734
DOI: 10.1055/a-2116-6734
special topic
C–H Bond Functionalization of Heterocycles
Rh-Catalyzed C–H Functionalization of the (Pyrazol-5-yl)pyridine Core of GBT-440
We thank Council of Scientific and Industrial Research (CSIR) for fellowships to RGK and SVH.
Abstract
The Rh-catalyzed cross dehydrogenative coupling (CDC)/alkylation of the pyrazolylpyridine unit of GBT-440 proceeded smoothly under ambient conditions and selectively on the pyrazole unit while directed by the pyridine. The scope of these reactions was established by employing simple as well as conjugated olefins for CDC and various diazo esters and the TIPS-EBX reagent for alkylation. At the outset, a focused small molecule library around the bis-heterocyclic core of GBT-440 was developed via C–H functionalization.
Key words
Rh catalysis - C–H activation - cross dehydrogenative coupling - GBT-440 - diazo ester - TIPS-EBXSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2116-6734.
- Supporting Information
Publication History
Received: 10 April 2023
Accepted after revision: 22 June 2023
Accepted Manuscript online:
22 June 2023
Article published online:
08 August 2023
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