反应详情

温度

80 °C

A three necked flask was charged with methyl 4-bromo-3-methylbenzoate (2.18 mmol), bis(pinacolato)diboron (2.29 mmol), palladium acetate (0.065 mmol), potassium acetate (6.54 mmol) and DMF (10 ml). The solution was degassed by bubbling through N2 gas for 30 mins and was then heated to 80° C. under N2 for 3 h. Reaction was then cooled to room temperature and 4-(5-Bromo-furan-2-ylmethyl)-morpholine (2.18 mmol), cesium carbonate (3.27 mmol) and Pd(PPh3)4 (0.065 mmol) added. The reaction was heated to 80° C. and stirred for a further 17 h. Mixture was then diluted with EtOAc and water and filtered through a celite pad to remove black particulates. The organic layer was separated, washed with brine and dried over Na2SO4 and concentrated in vacuo. Flash chromatography of the residue (silica, 10-99% EtOAc in hexane) gave 3-Methyl-4-(5-morpholin-4-ylmethyl-furan-2-yl)-benzoic acid methyl ester as a grey powdery solid: m/z in MS ES+=316 [M+H]+, 0.51 mmol, 23%.

1. customThe solution was degassed
2. customby bubbling through N2 gas for 30 mins
3. customReaction
4. temperaturewas then cooled to room temperature
5. temperatureThe reaction was heated to 80° C.
6. filtrationfiltered through a celite pad
7. customto remove black particulates
8. customThe organic layer was separated
9. washwashed with brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated in vacuo