Cesium carbonate → HCID 22959423, compound

Temperature

100 °C

To the mixture of sodium (((2,4-dichlorobenzyl)oxy)methyl)trifluoroborate (50 mg, 0.18 mmol) synthesized in Example 8 and 1,4-dioxane (1.5 ml), water (0.15 ml), cesium carbonate (170 mg, 0.53 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (15 mg, 0.036 mmol), and palladium(II) acetate (4.0 mg, 0.018 mmol) were added at room temperature, and the obtained reaction mixture was then stirred at 100° C. (an outer temperature) for 8.5 hours. The reaction mixture was cooled to room temperature, and then water and dichloromethane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1), thereby obtaining the entitled compound (1.1 mg, 4%).

1. additionwere added at room temperature
2. customthe obtained reaction mixture
3. temperatureThe reaction mixture was cooled to room temperature
4. filtrationfollowed by filtration with Celite
5. customThe organic layer of the filtrate was separated
6. washwashed with saturated saline
7. customThe solvents were evaporated under reduced pressure from the organic layer
8. customthe obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1)

ORD record

ord-300cd4a73cf344c5ba39d72f697a1ee6

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273885B2