Methyl 2,6-dichloroisonicotinate → Methyl 2-chloro-6-methanesulphonylamino-isonicotinate

HRID 1436584ノート

反応式

HRID 1436584 の反応式
[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]=1

参加物

6

反応物 3

HCID 93237Methyl 2,6-dichloroisonicotinateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 13150714Methanesulfonamide sodium salt

生成物 1

HCID 86615008Methyl 2-chloro-6-methanesulphonylamino-isonicotinate収率 50%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  1. customflushed with nitrogen
  2. temperatureHeat
  3. temperatureCool the mixture to room temperature
  4. filtrationfilter through a pad
  5. filtrationof filtering agent
  6. washwash the solid with dichloromethane
  7. concentrationConcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-1f11e7d59e244effaaeb62fb8582107d
出典データセット
uspto-grants-2009_11
特許番号
US07618978B2

反応ノート

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