Chlorosuccinimide → 3-chloro-4-[(2,4-difluorobenzyl)oxy]-1-(2,6-difluorophenyl)-6-(hydroxymethyl)pyridin-2(1H)-one

HRID 1832041Notes

Reaction equation

HRID 1832041 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[N:9]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])[C:8](=[O:22])[CH:7]=1.[Cl:28]N1C(=O)CCC1=O>C(#N)C>[Cl:28][C:7]1[C:8](=[O:22])[N:9]([C:14]2[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=2[F:20])[C:10]([CH2:12][OH:13])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 22050497HCID 22050497, compound

Product 1

HCID 220506833-chloro-4-[(2,4-difluorobenzyl)oxy]-1-(2,6-difluorophenyl)-6-(hydroxymethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by taking 4-[(2,4-difluorobenzyl)oxy]-1-(2,6-difluorophenyl)-6-(hydroxymethyl)pyridin-2(1H)-one (1.5 g, 3.9 mmol) in acetonitrile (15 mL) and adding to that N-chlorosuccinimide (580 mg, 4.3 mmol). The reaction was stirred at rt for 3 h afterwhich a small amount of additional N-chlorosuccinimide (50 mg, 0.4 mmol) was added to the reaction. Stirring was continued for 1 h. The reaction mixture was filtered through a fritted funnel to obtain the crude material. 1H NMR (400 MHz, DMSO-d6) δ 7.69-7.61 (m, 2H), 7.37-7.31 (m, 3H), 7.17 (dt, J=8.8, 2.0 Hz, 1H), 6.80 (s, 1H), 5.70 (t, J=6.0 Hz, 1H), 5.38 (s, 2H), 4.01 (d, J=6.0 Hz, 2H); ES-HRMS m/z 414.0515 (M+H calcd for C19H13ClF4NO3, requires 414.0520).

Workup

  1. additionwas added to the reaction
  2. filtrationThe reaction mixture was filtered through a fritted funnel

Sources & evidence

ORD record
ord-17902e3fc3094c4786a1c2debbcce426
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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