Sodium Azide → HCID 59519478, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-acetyl-5-chloro-4-fluoro-3-(2-fluorophenylamino)picolinate (WO 2005/051906) (2 g, 5 mmole) in a mixture of acetone (36 ml) and H2O (12 ml) is added NaN3 (487 mg, 7.5 mmol). The reaction is heated at 65° C. for 16 h and cooled to room temperature. Acetone is concentrated and the resulting mixture is extracted with EtOAc (2×50 ml). The combined organic solution is washed with brine (50 ml), dried over MgSO4 and concentrated to give a yellow solid. To the solid is added H2O (24 ml) and the reaction is heated at reflux for 3 h. The reaction is cooled to room temperature, filtered, and washed with H2O. The resulting solid is dried under high vacuum with P2O5 at 65° C. for 24 h to give the title compound.

Provenance & Evidence