[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.Cl[C:22]1[N:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]1([C:22]2[N:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Phenylboronic acid (4630.9 mg, 37.98 mmol), K3PO4 (20129 mg, 94.95 mmol), and PdCl2(dppf).CH2Cl2 (1291 mg, 1.58 mmol) was added to a solution of 2-(6-chloropyridin-3-yl)acetonitrile (5000 mg, 31.65 mmol) in dioxane (100 mL) and H2O (10 mL). The resulting mixture was stirred at 75° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 2-(6-phenylpyridin-3-yl)acetonitrile: LCMS tR=1.15 Min (5 min run, UV254nm), Mass calculated for, M+194.0, observed LC/MS m/z 195.0 (M+H).
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