Réaction #1483621

Équation de réaction

2-bromo-3-methoxy-6-nitropyridine

4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

potassium phosphate tribasic

DMA

→

3-methoxy-6-nitro-2-(prop-1-en-2-yl)pyridine

Rendement 66.0%

Solvants

ethyl acetate

brine

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONIn a microwave vial was added
2. 2
   AutreThe vial was sealed
3. 3
   Températurecooled
4. 4
   AutreThe organic phase was separated
5. 5
   Lavagewashed with brine (3×)
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Autrepurified by chromatography (silica, 5 to 35% ethyl acetate in hexanes)

Mode opératoire

In a microwave vial was added a mixture of 2-bromo-3-methoxy-6-nitropyridine (1.5 g, 6.44 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (1.41 g, 8.37 mmol), tetrakis(triphenylphosphine)palladium (0) (744 mg, 644 μmol), potassium phosphate tribasic (2.73 g, 12.9 mmol), DMA (16.1 mL) and water (5.36 mL). The vial was sealed and heated in the microwave for 20 min at 150° C., then cooled and diluted with ethyl acetate and brine. The organic phase was separated and washed with brine (3×), then concentrated in vacuo and purified by chromatography (silica, 5 to 35% ethyl acetate in hexanes) to give 3-methoxy-6-nitro-2-(prop-1-en-2-yl)pyridine (824 mg, 4.24 mmol, 66%) as a brown solid. MS (EI/CI) m/z: 194.8 [M+H].

Source