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CC BY 4.0 · SynOpen 2024; 08(01): 76-82
DOI: 10.1055/a-2266-3213
paper

Regioselective C3-Formylation of 2H-Indazoles Using Selectfluor under Microwave-Assisted Conditions

Manivel Pitchai∗
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Mahammed Kaspady
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Gopikumar Indasi
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Rajesh Krishnan
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Gururaju Sannakki Maheswarappa
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Muthalagu Vetrichelvan  ∗
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Arvind Mathur
b   Small Molecule Drug Discovery, Bristol Myers Squibb Research and Early Development, P.O. Box 5400, Princeton, NJ 08543-4000, USA
,
Anuradha Gupta
b   Small Molecule Drug Discovery, Bristol Myers Squibb Research and Early Development, P.O. Box 5400, Princeton, NJ 08543-4000, USA
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Abstract

An efficient microwave-assisted Selectfluor-mediated regioselective C3-formylation of 2H-indazoles bearing a variety of alkyl and aryl substituents using DMSO as the formylating agent has been developed. This methodology provides access to 3-formyl 2H-indazoles with moderate to excellent yields. These functionalized indazoles are potentially useful as templates for drug discovery. Control experimental results suggest that this formylation probably proceeds through a radical pathway.

Key words

2H-indazoles - Selectfluor - C3-formylation - microwave - radical pathways

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2266-3213. Spectral data for the new intermediates are presented.
  • Supporting Information


Publication History

Received: 18 August 2023

Accepted after revision: 09 February 2024

Accepted Manuscript online:
12 February 2024

Article published online:
04 March 2024

© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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