[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[C:9]1([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Dissolving 5.5 g (32 mmol) of 2-amino-5-bromopyridine, 4.3 g (32 mmol) of phenylboronic acid and 0.80 g of tetrakis (triphenylphosphine) palladium into 100 milliliter of 1,2-dimethoxyethane, adding 50 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 8 hours. After completion of the reaction and after filtration of the solution, washing the organic layer with water, dried it with the use of sodium sulfate. Removing the solvent by distillation, 6.2 g of crude 5-phenyl-2-amino-pyridine was obtained.
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