[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:12]1[C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=[CH:14][N:13]=1)[C:9](=[O:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.C([O-])(O)=O.[Na+].[Pd](Cl)Cl>[C:9]([N:8]1[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:17]=2[CH:18]=[CH:19][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:20][C:6]=2[CH2:7]1)(=[O:11])[CH3:10]To a stirred mixture of N-(5-Bromo-2-iodo-benzyl)-N-(3-vinyl-pyridin-2-yl)-acetamide E (60.0 mg, 0.13 mmol) and triethyl amine (55.0 μL, 0.39 mmol) in anhydrous DMF (1.4 mL) under argon was added Palladium dichloride (4.60 mg, 26 μmol). This mixture was heated at 65° C. for 1 h, cooled and diluted with saturated NaHCO3 solution (20 mL). The mixture was extracted with EtOAc (4×30 mL). The combined EtOAc extracts were washed with water (3×10 mL), brine (1×10 mL), dried (MgSO4), filtered and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 4 g column, eluted with CH2Cl2-EtOAc, detected at 254 nM to give 33 mg of 78F in 77% yield. HPLC Rt=3.04 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=329.
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