Potassium Phosphate, Tribasic → Methyl 2-chloro-6-methanesulphonylamino-isonicotinate

HRID 74583

Reaction equation

HRID 74583 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].[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.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]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:17][S:14]([CH3:13])(=[O:16])=[O:15])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 93237Methyl 2,6-dichloroisonicotinateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 86615008Methyl 2-chloro-6-methanesulphonylamino-isonicotinate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere 10 g (49 mmol) methyl 2,6-dichloro-isonicotinate, 5.6 g (59 mmol) methanesulphonamide, 14 g (68 mmol) potassium phosphate, 1.7 g (2.9 mmol) Xantphos and 0.90 g tris(dibenzylideneacetone)dipalladium in 300 mL dioxane were stirred for 5 h at 100° C. The mixture was suction filtered through kieselguhr and evaporated down. The residue was stirred with ethanol and the solid was suction filtered.

Workup

  1. filtrationfiltered through kieselguhr
  2. customevaporated down
  3. filtrationfiltered

Sources & evidence

ORD record
ord-37bf25dc5c344be7a2563033c75a27d7
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

Loading…