C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:23]([C:25]1[CH:26]=[C:27](Br)[CH:28]=[CH:29][CH:30]=1)[CH3:24].[C:32]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].CC(C)([O-])C.[Na+]>CCOCC.Cl[Pd]Cl.CCOC(C)=O.CCCCCC.C1(C)C=CC=CC=1>[C:32]([N:39]1[CH2:40][CH2:41][N:42]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH2:23][CH3:24])[CH:26]=2)[CH2:43][CH2:44]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]
Into a 15 mL round-bottomed flask fitted with a reflux condensor, a magnetic stirring bar, and a nitrogen inlet was added 1 mL dry toluene followed by 0.016 g (0.09 mmol) PdCl2 and 0.055 g (0.18 mmol) tri-o-tolylphosphine. After stirring for 15 min, an additional 15 mL dry toluene was added followed by 0.33 g (1.8 mmol) 3-ethylbromobenzene, 0.41 g (2.2 mmol) 1-Boc-piperazine and 0.242 g (2.5 mmol) sodium t-butoxide. The reaction was heated to reflux for 18 hr, after which time TLC (20% EtOAc/Hexane) showed the formation of a new spot. The reaction was cooled, diluted with 50 mL of ether, filtered through a Celite pad, and extracted with 3×10 mL water and 1×15 mL brine. The organic phase was dried (Na2SO4), filtered and the solvent removed in vacuo to get the crude product, which was purified by passing through a 2" silica pad (1% to 4% EtOAc/Hexane) to yield 1-Boc-4-(3-ethylphenyl)piperazine.
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