Dichloromethane → (Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-methoxybenzoate (Intermediate 161, 0.163 g), furan-3-yl boronic acid (0.041 g), palladium (II) chloride dppf complexed with DCM (0.025 g), cesium carbonate (0.282 g) in water (0.5 ml) and dioxane (3 ml) was degassed and then heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-5% to give (Z)-methyl 6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-3-(furan-3-yl)-2-methoxybenzoate as an orange oil.

Provenance & Evidence