Potassium Carbonate → N-(2-([1,1'-biphenyl]-3-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

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Reaction Conditions

Reaction Steps

A solution of N-(2-(3-bromophenyl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (30 mg, 0.064 mmol) and phenyl boronic acid (39 mgs, 0.32 mmol) in THF (1.2 mL) was degassed with nitrogen. Dichloro[1,1′ bis(di-tert-butylphosphino)]ferrocene palladium (II) (5 mgs, 0.006 mmol) and 1 M potassium carbonate (1.2 mL) were added. The reaction was heated overnight at 60° C. The reaction was extracted with ethyl acetate and dried over sodium sulfate. The crude was purified by prep TLC using 30% EA/hexanes to yield N-(2-([1,1′-biphenyl]-3-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (6 mgs, yield 18%). 1H NMR (300 MHz, CDCl3) δ 8.29 (s, 1H) 8.18 (d, J=7.2 Hz, 1H), 7.81 (d, J=7.2 Hz, 1H), 7.64-7.30 (m, 10H) 5.88 (s, 1H), 3.73 (d, J=7.2 Hz, 2H), 1.48 (s, 6H). MS (ESI) m/z: Calculated for C26H22F3N3O2: 465.17. found: 466.2 (M+H)+.

Provenance & Evidence