Methanesulfonyl chloride → HCID 18324382, compound

HRID 1251918Notes

Reaction equation

HRID 1251918 reaction equation
CS([Cl:5])(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[C:15]([CH3:23])[N+:14]=2[O-])=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[C:15]([CH2:23][Cl:5])[N:14]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18324528HCID 18324528, compound

Product 1

HCID 18324382HCID 18324382, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methane sulfonyl chloride (7.11 ml) was added to a stirred solution of 2-(4-fluorophenyl)-3-(methoxycarbonyl)-6-methylpyridine-1-oxide (12.0 g) in toluene (300 ml) and the mixture heated at reflux under an inert atmosphere for 16 hours. The solution was partially concentrated under reduced pressure and then applied directly to a silica flash column and eluted with ethyl acetate/iso-hexane (1:5) to give methyl 2-(4-fluorophenyl)-6-chloromethylpyridin-3-carboxylate as a white crystalline solid (13.6 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux under an inert atmosphere for 16 hours
  3. concentrationThe solution was partially concentrated under reduced pressure
  4. washeluted with ethyl acetate/iso-hexane (1:5)

Sources & evidence

ORD record
ord-6b89c4a55bb34dbe9f60acdde89ab5d7
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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