3-Pyridinylboronic acid → HCID 44561061, compound

HRID 1675516Notes

Reaction equation

HRID 1675516 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]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 112982573-bromo-2-methylcyclopent-2-enone

Product 1

HCID 44561061HCID 44561061, compoundYield 31%

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

  1. customPurification by automated flash chromatography
  2. washelution (0 to 100% ethyl acetate/hexanes) and further recrystallization

Sources & evidence

ORD record
ord-251d0e0eed1c473a97aab6ac37240103
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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