3-Pyridinylboronic acid → HCID 44561061, compound
Reaction equation
Br[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]=1[CH3:8].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1>>[CH3:8][C:3]1[C:4](=[O:7])[CH2:5][CH2:6][C:2]=1[C:11]1[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=1Participants
3
Procedure
Synthesized from 3-bromo-2-methylcyclopent-2-enone and 3-pyridine boronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (0 to 100% ethyl acetate/hexanes) and further recrystallization yielded the product (38 mg, 31%) as a brown oil. 1H NMR (CDCl3, 300 MHz): δ 8.78 (s, 1H), 8.63 (br d, J=3.6 Hz, 1H), 7.82 (dt, J=8.1, 2.1 Hz, 1H), 7.40 (dd, J=8.1, 4.8 Hz, 1H), 2.91-2.96 (m, 2H), 2.56-2.59 (m, 2H), 1.98 (t, J=2.1 Hz, 3H). 13C NMR (CDCl3, 75 MHz): δ 208.8, 162.5, 150.1, 148.3, 137.9, 134.5, 129.1, 123.4, 33.9, 29.0, 9.9. LCMS (ESI): mass calcd for (C11H11NO) m/z 173.08; measured [M+H]+: m/z 174.07.
Workup
- customPurification by automated flash chromatography