4-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one → HCID 54724162, compound

HRID 1867018Notes

Reaction equation

HRID 1867018 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)C1C=CC=CC=1>C(O)C>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][N:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]1=[O:23]

Participants

3

Reactant 1

HCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

Product 1

HCID 54724162HCID 54724162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a Fischer-Porter bottle, added a solution of 4-(benzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one (4.5 g, 14.56 mmol) in absolute ethanol (20 mL). Flushed the solution with nitrogen then added palladium catalyst (1.05 g, 10% Pd/C). Sealed bottle and evacuated system. The system was purged with hydrogen gas (2×15 psi) to check for leaks. The reaction was charged with hydrogen (35 psi) and stirred at room temperature for 45 minutes. The system was evacuated and flushed with nitrogen. The reaction was filtered and the catalyst was carefully washed with fresh ethanol. The filtrate was concentrated under reduced pressure 1H-NMR (CD3OD, 400 MHz) δ7.54 (d, 1H, J=7.6 Hz), 7.32 (m, 1H), 7.06 (d, 1H, J=7.6 Hz), 6.99 (m, 2H), 6.05 (dd, 1H, J=2.4 Hz, 2.8 Hz), 5.83 (d, 1H, J=2.4 Hz), 5.09 (s, 2H); ES-HRMS m/z 220.0774 (M+H calculated for C12H11NO2F requires 220.0787).

Workup

  1. customFlushed the solution with nitrogen
  2. customSealed bottle
  3. customevacuated system
  4. customThe system was purged with hydrogen gas (2×15 psi)
  5. additionThe reaction was charged with hydrogen (35 psi)
  6. customThe system was evacuated
  7. customflushed with nitrogen
  8. filtrationThe reaction was filtered
  9. washthe catalyst was carefully washed with fresh ethanol
  10. concentrationThe filtrate was concentrated under reduced pressure 1H-NMR (CD3OD, 400 MHz) δ7.54 (d, 1H, J=7.6 Hz), 7.32 (m, 1H), 7.06 (d, 1H, J=7.6 Hz), 6.99 (m, 2H), 6.05 (dd, 1H, J=2.4 Hz, 2.8 Hz), 5.83 (d, 1H, J=2.4 Hz), 5.09 (s, 2H)

Sources & evidence

ORD record
ord-3be8d979744842c2a67ea80f878cec01
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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