3-Pyridinylboronic acid → 3-(Pyridin-3-yl)cyclohex-2-en-1-one

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Reaction Steps

Prepared as described above from 3-bromocyclohex-2-enone and 3-pyridinylboronic acid. Purification by automated flash chromatography using gradient elution (20 to 60% ethyl acetate/hexanes) yielded the product (42 mg, 54%) as a dark orange solid. 1H NMR (300 MHz, CDCl3): δ 7.80 (ddd, J=7.8, 2.4, 1.5 Hz, 1H), 7.34 (ddd, J=7.8, 4.5, 0.6 Hz, 1H), 6.41 (t, J=1.5 Hz, 1H), 2.78 (t, J=5.8 Hz, 2H), 2.51 (t, J=6.6 Hz, 2H), 2.19 (quintet, J=6.2 Hz, 2H). 13C (75 MHz, CDCl3): 199.2, 156.5, 150.8, 147.3, 133.4, 126.6, 123.6, 37.4, 28.0, 22.9. LCMS (ESI): mass calcd for (C11H11NO) m/z 173.08; measured [M+H]+: m/z 174.16.

Provenance & Evidence