[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[CH:4][CH:3]=1Combine 4-bromophenylboronic acid (6.064 g, 30.195 mmol), 2-iodo-phenylamine (5.532 g, 25.257 mmol), toluene, 2N Na2CO3 (13 ml, 26 mmol), and tetrakis(triphenyl-phosphine)palladium(0) (0.849 g) and heat to 80° C. After 4 hours cool to room temperature and stir for 16 hours. Dilute the reaction with EtOAc and back extract water layer with EtOAc. Combine the organic layers and wash with H2O, and dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography (silica gel), eluting with first hexane and increasing up to 10% EtOAc/Hexane to afford 4′-bromo-biphenyl-2-ylamine (4.008 g, 64%). LCMS 247.
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