Nitrogen → 6-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-2-methyl-benzofuran-3-carboxylic acid methyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran-3-carboxylic acid methyl ester (0.145 g, 0.459 mmol) and 4-(4-bromo-3-methyl-phenoxymethyl)-5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole (229 mg, 0.504 mmol) in toluene (5 mL) is evacuated and refilled with N2 three times. Pd(OAc)2 (10 mg), 2-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl (38 mg) and potassium phosphate, tribasic, N-hydrate (195 mg) in water (0.5 mL) are added. The resulting mixture is evacuated and refilled with N2 three times and stirred at 110° C. for 16 hours. The mixture is cooled to room temperature and filtered through a pad of diatomaceous earth. The filtrate is concentrated to a residue. The residue is purified via silica gel chromatography eluting with 25% EtOAc/Hexanes to provide the title compound (0.14 g, 55%). 1H NMR (400 MHz, CDCl3): 7.90 (d, 1H), 7.39 (d, 1H), 7.37 (s, 1H), 7.31-7.29 (m, 2H), 7.18 (d, 1H), 7.10 (d, 1H), 6.70-6.66 (m, 2H), 4.80 (s, 2H), 3.94 (s, 3H), 2.76 (s, 3H), 2.18 (s, 3H), 2.17 (m, 1H), 1.29-1.25 (m, 2H), 1.15-1.11 (m, 2H).

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