Réaction #40448

Équation de réaction

5-chloroisatoic anhydride

2-amino-5-chloropyridine

potassium bis(trimethylsilyl)amide

toluene

→

(2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was warmed up
2. 2
   workup.STIRRINGstirred overnight
3. 3
   ConcentrationAfter concentrated
4. 4
   Lavagethe crude was washed with saturated ammonium chloride solution
5. 5
   Extractionextracted by ethyl acetate
6. 6
   SéchageThe organic layer was dried over magnesium sulfate
7. 7
   Concentrationconcentrated

Mode opératoire

To a solution of 2-amino-5-chloropyridine (787 mg, 6.1 mmol) in tetrahydrofuran (5 ml) was added 0.5M potassium bis(trimethylsilyl)amide in toluene (20 ml, 10.1 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (1 g, 5.1 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After concentrated, the crude was washed with saturated ammonium chloride solution and extracted by ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide as yellow solid (1.39 g. 99%). MS found for C12H9Cl2N3O M+=282, (M+2)+=284.

Source