Metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines

Add time:08/02/2019    Source:sciencedirect.com

Mono- and disubstituted 2-bromo-3-fluoroquinolines 3 are readily accessible. They can be converted into the 3-fluoroquinoline-2-carboxylic acids 5 by consecutive halogen/metal permutation and into the 2-bromo-3-fluoroquinoline-4-carboxylic acids 6 by consecutive deprotonation and carboxylation. The latter compounds can be reduced to afford the 3-fluoroquinoline-4-carboxylic acids 7. The yields are excellent throughout. Rather than to introduce one functional group alternatively at the 2- or 4-position, one may also attach two different functional groups sequentially to both sites.

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