Réaction #2058787

Équation de réaction

2-Bromo-3-methoxy-6-nitro-pyridine

1,4-benzodioxane-6-boronic acid

dimethylacetamide water

potassium phosphate

→

2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-methoxy-6-nitro-pyridine

Solvants

ethyl acetate

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added to a microwave tube
2. 2
   workup.ADDITIONThe solution was added in a separating funnel
3. 3
   AutreThe organic layer was separated
4. 4
   Extractionthe aqueous was extracted again with ethyl acetate
5. 5
   LavageThe combined organics were washed with water (*2)
6. 6
   Séchagebrine, dried over magnesium sulphate
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe crude was used without further purification (0.48 g, 77%)

Mode opératoire

2-Bromo-3-methoxy-6-nitro-pyridine (0.5 g, 2.14 mmol), 1,4-benzodioxane-6-boronic acid (0.5 g, 2.79 mmol) and a mixture of dimethylacetamide/water (10 mL/3 mL) were added to a microwave tube containing potassium phosphate (0.91 g, 4.29 mmol) and palladium tetrakistriphenylphosphine (0.4 g, 0.2 mmol) and the reaction was heated to 150° C. for 10 min. The solution was added in a separating funnel and water and ethyl acetate were added. The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organics were washed with water (*2) then brine, dried over magnesium sulphate and concentrated in vacuo. The crude was used without further purification (0.48 g, 77%). LCMS Method: 2: RT: 4.41 min, MI: 289 [M+1].

Source