Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[NH:7][CH2:8][CH3:9].[O:12]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:8]([NH:7][C:6]1[CH:10]=[C:2]([C:14]2[CH:15]=[CH:16][O:12][CH:13]=2)[CH:3]=[CH:4][C:5]=1[CH3:11])[CH3:9]0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%).
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