3-Bromocyclohex-2-enone → 3-(Quinolin-6-yl)cyclohex-2-enone

Participants

Reaction Steps

Synthesized from 3-bromocyclohex-2-enone and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (40 to 100% ethyl acetate/hexanes) yielded the product (164 mg, 88%) as a white powder. 1H NMR (CDCl3, 300 MHz): δ 8.92 (dd, J=4.2, 1.5 Hz, 1H), 8.17 (d, J=7.8 Hz, 1H), 8.11 (d, J=9.0 Hz, 1H), 7.95 (d, J=2.1 Hz, 1H), 7.86 (dd, J=9.0, 2.4 Hz, 1H), 7.43 (dd, J=8.4, 4.5 Hz, 1H), 6.54 (s, 1H), 2.89 (t, J=6.3 Hz, 2H), 3.53 (t, J=6.3 Hz, 2H), 2.21 (pent, J=6.3 Hz, 2H). 13C NMR (CDCl3, 75 MHz): δ 199.4, 158.3, 151.2, 148.6, 136.7, 136.5, 129.9, 127.8, 126.8, 126.3, 125.7, 121.7, 37.3, 28.2, 22.8. LCMS (ESI): mass calcd for (C15H13NO) m/z 223.10; measured [M+H]+: m/z 224.80.

Provenance & Evidence