Methyl iodide → 1-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-methoxy-5-trifluoromethyl-phenyl)-2-methyl-isothiourea

Participants

Reaction Conditions

Reaction Steps

(Reaction performed under N2 atmosphere) NaH (1.267 g, 0.05279 mol) was added portionwise to an ice-cooled solution of intermediate D5 (21.32 g, 0.05279 mol) in THF (480 ml) and the resulting mixture was stirred for 15 minutes at 0° C. Subsequently, a solution of CH3I (7.493 g, 0.05279 mol) in THF (40 ml) was added dropwise and the mixture was stirred for 2 hours at room temperature. Then the reaction mixture was quenched with H2O and extracted with CH2Cl2 (3×500 ml). The organic layers were separated, combined, washed with brine, dried (MgSO4), filtered and the solvent was evaporated in vacuo. The crude product was triturated with DIPE/heptane. The off-white solid was filtered off and dried to yield 16.203 g of intermediate D6 (73.5%). Heptane and H2O were added to the filtrate and this mixture was stirred overnight at room temperature. The off-white precipitate was filtered off and dried to yield more (1.957 g) of intermediate D6 (9%).

Provenance & Evidence