Methyl 2,6-dichloroisonicotinate → Methyl 2-chloro-6-methanesulphonylamino-isonicotinate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Cl)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[Na+].[CH3:35][S:36]([NH-:39])(=[O:38])=[O:37]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[C:10]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])[N:11]=[C:2]([Cl:1])[CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Add methyl 2,6-dichloro-isonicotinate (2.06 g, 10.0 mmol), toluene (10 mL), tris(dibenzylideneacetone)dipalladium(0) (0.458 g, 0.50 mmol), 2-(di-tert-butylphosphino)biphenyl (0.298 g, 1.00 mmol), and methanesulfonamide sodium salt (1.17 g, 10.0 mmol) to a sealed flask flushed with nitrogen. Heat and stir the sealed flask at 100° C. for 18 h. Cool the mixture to room temperature and filter through a pad of filtering agent, and wash the solid with dichloromethane. Concentrate and purify (silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes) to give the title compound (1.31 g, 50%).
Workup
- customflushed with nitrogen
- temperatureHeat
- temperatureCool the mixture to room temperature
- filtrationfilter through a pad
- filtrationof filtering agent
- washwash the solid with dichloromethane
- concentrationConcentrate
- custompurify
- wash(silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes)
Sources & evidence
- ORD record
- ord-55a4bf6278f24b4e896c594621a66152
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585885B2
Reaction notes
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