One‐Pot Sequential Bromination and Fluorination to Access 3‐Fluoroimidazo[1,2‐a]pyridines from Arylketones

3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were selectively synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The sequence of reactions involved bromination, condensation, and late‐stage fluorination. Two halogenating reagents play key roles in the process. We found t...

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Veröffentlicht in:European journal of organic chemistry 2018-07, Vol.2018 (26), p.3432-3436
Hauptverfasser: Udavant, Rohini N., Yadav, Ashok R., Shinde, Sandip S.
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Sprache:eng
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Zusammenfassung:3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were selectively synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The sequence of reactions involved bromination, condensation, and late‐stage fluorination. Two halogenating reagents play key roles in the process. We found that tetrabutylammonium tribromide and SelectfluorTM gave excellent yields of the desired products in the one‐pot sequential reaction. 3‐Fluoro‐2‐arylimidazo[1,2‐a]pyridines were synthesised in one‐pot from acetophenones and 2‐aminopyridines under mild conditions. The reaction sequence involves bromination, condensation, and fluorination steps. The halogenating reagents TBATB (tetrabutylammonium tribromide), and SelectfluorTM play key roles without interfering with the other steps.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800578