4-Fluorophenylboronic acid → [7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3.00 g (8.62 mmol) (7-iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 20 ml dioxane and 60 ml 1,2-dimethoxyethane were added 731 mg (17.2 mmol) lithium chloride, 299 mg (0.26 mmol) tetrakis(triphenyl-phosphine)palladium(0), 1.45 g (10.3 mmol) para-fluorobenzeneboronic acid and 18 ml of a 1 N aq. solution of sodium bicarbonate. The mixture was heated at 100° C. for 24 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 2.67 g (98%) [7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester as an off-white solid. ES-MS m/e (%): 317 (M+H+, 100).

Provenance & Evidence