Réaction #1483615

Équation de réaction

2-Bromo-3-methoxy-6-nitropyridine

cesium fluoride

2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

2-allyl-3-methoxy-6-nitropyridine

Rendement 75.0%

Solvants

THF

water

ethyl acetate

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled
2. 2
   AutreThe phases were separated
3. 3
   Lavagethe organic phase was washed with water (2×) and brine
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Autrepurified by chromatography (silica, 10 to 50% ethyl acetate in hexanes)

Mode opératoire

2-Bromo-3-methoxy-6-nitropyridine (3.22 g, 13.8 mmol), cesium fluoride (6.3 g, 41.5 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.6 g, 1.38 mmol) were combined with 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.55 g, 2.85 mL, 15.2 mmol) in THF (27 mL) and heated at 66° C. for 20 h. The mixture was cooled then diluted with water and ethyl acetate. The phases were separated then the organic phase was washed with water (2×) and brine, concentrated in vacuo and then purified by chromatography (silica, 10 to 50% ethyl acetate in hexanes) to give 2-allyl-3-methoxy-6-nitropyridine (2.0 g, 10.3 mmol, 75%) as a blue solid. MS (EI/CI) m/z: 194.8 [M+H].

Source