Estragole → N-(3,5-Bis-trifluoromethyl-benzyl)-6-[3-(4-methoxy-phenyl)-propyl]-N-methyl-4-o-tolyl-nicotinamide

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Reaction Steps

Deoxygenation of a solution of 89 mg (0.58 mmol) 4-allylanisole in 3 ml tetrahydrofuran by three freeze-thaw cycles was followed by addition of 73 mg (0.29 mmol) 9-borabicyclo[3.3.1]nonane dimer at room temperature under an atmosphere of argon. After 1.5 h 43 mg (0.58 mmol) potassium methoxide were added, and stirring was continued for 20 min. In one portion 250 mg (0.432 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4) were added, followed by a suspension of 10 mg (0.043 mmol) palladium(II) acetate and 37 mg (0.086 mmol) 1,3-bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride in 0.5 ml tetrahydrofuran. The reaction mixture was heated at reflux for 2 h. Cooling to room temperature was followed by dilution with tert-butyl methyl ether and washing with two portions of 1 M aqueous sodium hydroxide solution. The combined aqueous layers were extracted with tert-butyl methyl ether. The combined organic extracts were dried with magnesium sulfate and concentrated. Column chromatography afforded 184 mg (71%) of the title compound as a light-yellow amorphous mass.

Provenance & Evidence