4-Methylpyridine-3-Boronic Acid → 5-((4-Methylpyridin-3-yl)methyl)-2-phenylpyridine

Participants

Reaction Steps

Synthesized using compound 61a (100 mg, 0.40 mmol) and 4-methylpyridine-3-boronic acid (83 mg, 0.61 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using ethyl acetate as eluent. After flash chromatography the product was solved in ethyl acetate and a few drops of conc. HCl and water were added. After stirring for 30 minutes the phases were separated and water phase was neutralized with aqueous Na2CO3-solution (2M). After extraction with ethyl acetate and drying over MgSO4 the solvent was removed under vacuum. Light yellow solid. Yield: 54 mg, 52%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=2.22-2.29 (m, 3H), 4.02 (s, 2H), 7.11 (d, J=5.0 Hz, 1H), 7.37-7.51 (m, 4H), 7.64 (dd, J=8.2, 0.6 Hz, 1H), 7.95-8.01 (m, 2H), 8.38-8.46 (m, 2H), 8.52-8.57 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=19.3, 33.8, 120.5, 125.7, 126.9, 129.0, 129.1, 133.2, 133.8, 136.8, 139.2, 146.1, 148.7, 149.9, 150.7, 155.9; (ESI): m/z=260.85 [M+H]+.

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