Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=1To a solution of 3-bromopyridine (4.75 gm, 30 mmol) and 3-aminopyridine (1.88 gm, 20 mmol) in dry toluene (8 mL) was added sodium t-butoxide (2.3 gm, 24 mmol), tris(dibenylideneacetone) dipalladium(0) (63 mg, 0.069 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (XANTPHOS) (183 mg, 0.317 mmol). The vessel was capped with a septum, degassed (3×), and heated at 100 C for ˜24 hours. The cooled reaction was diluted with methylene chloride, washed with NaHCO3 solution, water, and the organic layer dried over anhydrous sodium sulfate, filtered and the solvent concentrated to a small volume. Upon addition of diethyl ether and a few drops of methanol the product precipitated. After stirring this mixture for ˜15 hours the purified product was isolated by filtration to give 2.89 gm (84% yield) of the title compound.
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