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ChemicalBook CAS DataBase List N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide synthesis

2synthesis methods
-

Yield:1293987-69-5 86%

Reaction Conditions:

with potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in dimethyl sulfoxide at 80; for 6 h;

Steps:

29.2

3-Bromo-N-methylbenzenesulfonamide (1.6 g, 6.39 mmol) was dissolved in anhydrous DMSO (21 mL) and then potassium acetate (1.57 g, 15.99 mmol) and bis(pinacolato)diboron (1.63 g, 6.39 mmol) were added. After flowing nitrogen to the reaction mixture for 10 minutes, Pd(dppf)2Cl2 (522 mg, 0.64 mmol) was added. The reaction mixture was stirred at 80 °C for 6 hours, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (10% ethyl acetate/hexane) yielded the target compound (1.65 g, 86% yield). [0366] MS m/z: 298.52 [M+1].

References:

WO2011/49332,2011,A2 Location in patent:Page/Page column 38