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

HRID 1675500Notes

Reaction equation

HRID 1675500 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1>>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 134025713-(Pyridin-3-yl)cyclohex-2-en-1-oneYield 54%

Procedure

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.

Workup

  1. customPrepared
  2. customPurification by automated flash chromatography
  3. washelution (20 to 60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-24b90e57c4c445939192fab2979657d0
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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