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Synthesis 2023; 55(21): 3600-3609
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

Rupali G. Kalshetti
a   Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
,
Swapnil V. Halnor
a   Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
,
Chepuri V. Ramana  ∗
a   Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
› Author AffiliationsWe thank Council of Scientific and Industrial Research (CSIR) for fellowships to RGK and SVH.
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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-EBX

Supporting 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

© 2023. Thieme. All rights reserved

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