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ChemicalBook CAS DataBase List N-(3-cyanopyridin-2-yl)-N-methylmethanesulfonamide
73161-37-2

N-(3-cyanopyridin-2-yl)-N-methylmethanesulfonamide synthesis

3synthesis methods
-

Yield:73161-37-2 93%

Reaction Conditions:

Stage #1: N-methylmethane sulphonamidewith potassium-t-butoxide in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2: 2-fluoro-nicotinonitrile at 80; for 2 h;

Steps:



To N-methylmethanesulfonamide (2.18 g, 20 mmol, 1.0 eq) in 20 mL of DMF, was added t-BuOK (2.24 g, 20 mmol, 1.0 eq.). After stirring at r.t. for 30 min., 2-fluoro-3-cyano-pyridine (2.44 g, 20 mmol, 1.0 eq) was added in one portion, and the resulting mixture was heated to 80 °C for 2 hr. (TLC showed the complete reaction). The reaction mixture was poured on ice and extracted with ethyl acetate. The dried organic layer was concentrated, and purified by column chromatography on silica gel with petroleum ether/ethyl acetate (v/v 1/1) as eluent, giving N-(3- cyano-2-pyridyl)- N-methyl-methanesulfonamide (4.0 g, 93%).

References:

WO2019/46163,2019,A1 Location in patent:Paragraph 00276