Pyridine → 3-(3-chloropropyl)-1-phenyl-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-chloropropyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.46 g, 1.75 mmol) in dichloromethane (10 mL) was treated with pyridine (0.16 mL, 2.6 mmol), phenylboronic acid (0.43 g, 3.5 mmol) and copper(II) acetate (0.48 g, 2.6 mmol) and stirred at 23° C. for 16 hours. The reaction mixture was quenched by the addition of ammonium hydroxide (10 mL), diluted with methanol (2.0 mL), extracted with dichloromethane (3×10 mL), dried (Na2SO4), and evaporated. Flash chromatography (SiO2, 3-40% ethyl acetate/hexanes) provided 3-(3-chloropropyl)-1-phenyl-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.055 g, 9.4%) as a yellow film:

Provenance & Evidence