3-Methylpyridine → Cyantraniliprole

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 2003/015519 for a method of preparation) (97.4% purity, 15.4 g, 49.6 mmol) and 2-amino-5-cyano-N,3-dimethylbenzamide (10.0 g, 52.5 mmol) in acetonitrile (80 mL) was added 3-picoline (13.9 g, 148 mmol). The mixture was cooled to 15 to 20° C., and then methanesulfonyl chloride (8.2 g, 71.2 mmol) was added dropwise at 15 to 20° C. After 1 h, water (37.3 g) was added dropwise to the reaction mixture while maintaining the temperature at 15 to 20° C. After the addition was complete, the mixture was heated at 45 to 50° C. for 30 minutes, and then cooled to 15 to 25° C. for 1 h. The mixture was filtered and the solids collected were washed with acetonitrile-water (approximately a 5:1 mixture, 2×10 mL) and acetonitrile (2×10 mL), and then dried under nitrogen to afford 24.0 g (93.6% corrected yield based on an assay of 91.6%, with a water content of 6%) of the title compound as an off-white solid.

Provenance & Evidence