3-Pyridinylboronic acid → 2-Phenyl-5-(pyridin-3-ylmethyl)pyridine

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Reaction Steps

Synthesized using compound 61a (100 mg, 0.40 mmol) and 3-pyridineboronic acid (74 mg, 0.61 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (2:1) 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. Beige solid. Yield: 32 mg, 32%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.80 (s, 2H), 6.99-7.06 (m, 1H), 7.15-7.20 (m, 1H), 7.21-7.35 (m, 4H), 7.45 (d, J=8.2 Hz, 1H), 7.72-7.77 (m, 2H), 8.28 (dd, J=4.7, 1.3 Hz, 1H), 8.36 (d, J=1.9 Hz, 1H), 8.33 (d, J=1.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=35.9, 120.4, 123.6, 126.8, 128.7, 128.9, 133.6, 135.4, 136.2, 137.0, 139.0, 148.1, 149.9, 150.1, 155.9; (ESI): m/z=246.98 [M+H]+.

Provenance & Evidence