CC(C)(C)OC(=O)N1CCNCC1.Cc1ncccc1Br>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.[Na+].[Pd]>Cc1ncccc1N1CCN(C(=O)OC(C)(C)C)CC1
Palladium acetate (65 mg, 0.29 mmol) and RuPhos (271mg, 0.58mmol) were dissolved in toluene (10 mL), degassed and purged with nitrogen and warmed to 50°C for 15 minutes. In a separate vessel, were mixed 3-bromo-2-methyl pyridine (1.00g, 5.81 mmol), BOC-piperazine (1.08g, 5.81mmol), sodium tertbutoxide and toluene (17 mL). The mixture was degassed, purged with nitrogen and warmed to 50°C. The catalyst was transferred to the reaction vessel and the mixture degassed and purged with nitrogen. The reaction was heated at 100°C overnight under nitrogen. The mixture was filtered through GF/F paper, washing with MeOH. The filtrate was concentrated to provide a dark brown gum. The gum was purified by flash silica chromatography, elution gradient 30 to 80% EtOAc in heptane. Pure fractions were evaporated to provide the desired product as a gum (1.492g, 93%). Rf (1:1 EtOAc/heptane) 0.3
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