Reacción #67739

Ecuación de reacción

CH2Cl2

2-methoxyaniline

1-(benzo[d][1,3]dioxol-5-yl)-N-(6-bromopyridin-2-yl)cyclopropanecarboxamide

XANTPHOS

→

1-(benzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxyphenylamino)pyridin-2-yl)cyclopropanecarboxamide

Disolventes

triethylamine

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting material was cooled to room temperature
2. 2
   OtroThe solvent was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONThe resulting mixture was dissolved in dichloromethane
4. 4
   Lavadowashed with H2O
5. 5
   SecadoThe organic layer was dried over anhydrous Na2SO4
6. 6
   Otroevaporated under reduced pressure
7. 7
   OtroThe crude product was purified by column chromatography on silica gel

Procedimiento

To 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-bromopyridin-2-yl)cyclopropanecarboxamide (72 mg, 0.2 mmol), XANTPHOS (7.00 mg, 0.008 mmol), KtBuO (31 mg, 0.28 mmol), (DPPF)2PdCl2.CH2Cl2 (33.00 mg, 0.24 mmol), and 2-methoxyaniline (30 mg, 0.24 mmol), 1,4-dioxane (0.400 mL) and triethylamine (0.200 mL) were added. The reaction mixture was heated to 150° C. in a microwave reactor for 10 minutes. The resulting material was cooled to room temperature. The solvent was evaporated under reduced pressure. The resulting mixture was dissolved in dichloromethane and washed with H2O. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxyphenylamino)pyridin-2-yl)cyclopropanecarboxamide which was then treated with HCl in MeOH to form the HCl salt (2.4 mg, 0.0055 mmol, 2.7%). ESI-MS m/z calc. 403.1. found 404.5 (M+1)+; retention time 3.01 minutes.

Fuente