Dimethylformamide → Methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate

Participants

Reaction Conditions

Reaction Steps

To an ice cooled stirred solution of methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate (D62) (66 g, 0.27 mol) and triethylamine (56.86 ml, 0.40 mol) in dimethylformamide (500 ml) methanesulfonylchloride (23.15 ml, 0.29 mol) was added dropwise maintaining the temperature at 0° C. The reaction mixture was stirred at 0° C. for 3.5 h then methanesulfonyl chloride (6.3 ml, 0.037 mol) and triethylamine (18.9 ml, 0.135 mol) were added and the reaction mixture was stirred for 3 h at 0° C. After this time the formed solid was filtered off. Water (700 ml) was added to the filtrate. The formed solid was filtered off, washed with water (400 ml) and dried under vacuo to afford the title compound (D63) (80 g).

Provenance & Evidence