Chlorosuccinimide → 3-Chloro-4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)-1H-pyridin-2-one

HRID 1866924Notes

Reaction equation

HRID 1866924 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C:8](=[O:20])[CH:7]=1.[Cl:26]N1C(=O)CCC1=O>CC(O)=O>[Cl:26][C:7]1[C:8](=[O:20])[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22050302HCID 22050302, compound

Product 1

HCID 114744543-Chloro-4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(2,4-difluorobenzyloxy)-1-(3-fluorobenzyl)-1H-pyridin-2-one (0.15 g, 0.4 mmol) in AcOH (3 mL) was added N-chlorosuccinimide (70 mg, 0.5 mmol), and the reaction mixture was heated at reflux for 10 min. The reaction mixture was cooled room temperature and the solvent was removed under reduced pressure. 1H NMR (300, MHz, CDCl3) δ 7.60-7.50 (m, 1H), 7.45-7.20 (m, 2H), 7.10-6.80 (m, 5H), 6.16 (d, J=8 Hz, 1H), 5.21 (s, 2H), 5.15 (s, 2H). ESHRMS m/z 380.0641 (M+H C19H14ClF3NO2 requires 480.0660).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 10 min
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-27929818ee9645c5bba1cec7554a8947
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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