Potassium Carbonate → 4-(6-Chlorobenzo[c][1,2,5]oxadiazol-5-yl)aniline

Participants

Reaction Conditions

Reaction Steps

Palladium tetrakis-triphenylphosphine (37 mg, 32 μmol) was added to a degassed solution of bromide 94 (150 mg, 643 μmol) and boronate 84 (211 mg, 964 μmol) in dioxane:acetonitrile:water (9:9:2, 3.2 mL) and potassium carbonate (205 mg, 964 μmol). The resulting mixture was heated under argon at 95° C. with stirring for 1 h. The mixture was then cooled, diluted with dichloromethane (25 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 95 (35 mg, 22%) as a solid: LRESIMS m/z 246.0 [M+H]+, calcd. for C12H9Cl1N3O1 246.0.

Provenance & Evidence