Methanol → Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a slurry of methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate (5.0 g, 17.66 mmol, prepared as in Example 113) in chloroform (20 mL) under nitrogen was added N,N,N-diisopropylethylamine (3.72 mL, 26.49 mmol). 4-Methylbenzenesulfonyl chloride (4.04 g, 21.20 mmol) was added over 5 minutes and the reaction was heated to 40 degrees C. and stirred one hour. The completed reaction was cooled to 25 degrees C. and 1:1 methanol:water was added to precipitate the product which was filtered, washed with more 1:1 methanol:water and dried in vacuo. This afforded the desired product as a solid.

Provenance & Evidence