Fluorinated candidates can be of great interest in the pharmaceutical industry. However, the synthesis of these fluoro analogs often pose significant challenges due to safety hazards and/or costs of fluorinating reagents. The synthesis is particularly challenging for electron rich aromatics such as five member heterocycles. Tetramethylammonium fluoride (TMAF) is well known as an effective and mild fluorinating reagent in the literature. However, sourcing of anhydrous tetramethylammonium fluoride is difficult beyond gram quantities. In this presentation we share the challenges of generating a fluorinated heterocycle on pilot scale using the cost effective tetramethylammonium fluoride tetrahydrate (TMAF.4H<sub>2</sub>0).

Successful fluorination of a challenging heterocycle using anhydrous tetramethylammonium fluoride on pilot scale

256th National Meeting (2018)

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