Brc1ccncc1.OC1CCNC1>C1CCOC1.CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.C[Si](C)(C)[N-][Si](C)(C)C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li+].[Pd].[Pd]>OC1CCN(c2ccncc2)C1
In a 50 ml round bottomed flask THF (1 mL) was added to a mixture of 4-bromopyridine (1 g, 6.33 mmol), pyrrolidin-3-ol (0.662 g, 7.60 mmol),2-(dimethylamino)-2'-(dicyclohexylphosphino)biphenyl (0.249 g, 0.63 mmol) and Pd2(dba)3 (0.580 g, 0.63 mmol). To the slurry lithium bis(trimethylsilyl)amide (13.92 mL, 13.92 mmol) was added dropwise at 0 °C and the solution was refluxed at 65 °C overnight for 20 hrs. The reaction mixture was passed through celite, concentrated and column purified (0-20%MeOH/DCM) to obtain 0.447 mg of product.
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