Reevaluation of the 2-nitrobenzyl protecting group for nitrogen containing compounds: an application of flow photochemistry

• Chloe I. Wendell, Michael J. Boyd

• Vertex Pharmaceuticals Inc., 50 Northern Avenue, Boston, MA, United States

Photochemistry under continuous flow conditions has many potential benefits for photochemical reactions that are problematic in batch. The 2-nitrobenzyl moiety is a photolabile protecting group for nitrogen. However, N-deprotection is generally impractical and, therefore, has not been extensively adopted. This Letter reports significant improvements in the N-deprotection of the 2-nitrobenzyl group through the application of continuous flow photolysis. This procedure was applied to a variety of substrates including indoles, indazoles, pyrazoles and secondary amines. Significant improvement in yield, reaction time and scalability was observed under continuous flow conditions.

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