CB(O)O.[C:5]([O-])([O-])=O.[K+].[K+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([N+:32]([O-:34])=[O:33])[C:23]=1OS(C(F)(F)F)(=O)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1.O.CCOC(C)=O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:5][C:23]1[C:22]([N+:32]([O-:34])=[O:33])=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][C:13]=1[O:12][CH3:11]To a stirred solution of 4.92 g of MeB(OH)2, 33.9 g of K2CO3, 25.6 g of ethyl 3-methoxy-5-nitro-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate in 500 ml of THF and 50 ml of water was added 5.03 g of PdCl2 dppf and the mixture was stirred under argon atmosphere at 80° C. overnight. The mixture was diluted with AcOEt and water, filtered through Celite and the filtrate was extracted with AcOEt. The extract was washed successively with saturated NaCO3aq and saturated brine, dried over Na2SO4, and concentrated. The residue was purified on SiO2 column chromatography and the fractions containing the intended compound were concentrated. The resulting solid was washed with n-hexane and dried to give 12.9 g of the intended compound as a yellow solid.
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