Methylamine → HCID 16723055, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (241 mg, 0.69 mmol) in carbon tetrachloride (2 mL) was added N-bromosuccinimide (122 mg, 0.69 mmol) and 2,2′-azobis(2-methylpropionitrile) (11 mg, 0.07 mmol) and the reaction mixture was stirred for 18 h at 70° C. It was diluted with dichloromethane (10 mL) and washed with aqueous sodium hydrogencarbonate (1 N, 10 mL). The aqueous phase was extracted with dichloromethane and dried over sodium sulfate. The resulting crude material was suspended in methylamine solution (2 M in THF, 2.0 mL, 4.0 mmol) and potassium carbonate (110 mg, 0.80 mmol) was added. The reaction mixture was stirred for 2 h at 50° C. The mixture was diluted with ethyl acetate (20 ml), washed twice aqueous sodium carbonate (half saturated) and was extracted with ethyl acetate. Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:40:20:0 to 0:75:20:5) afforded the title compound (119 mg, 46%) as a white solid. MS: m/e=381.2 [M+H]+.

Provenance & Evidence