Water → HCID 70818258, compound

Temperature

100 °C

Under argon atmosphere, sodium carbonate (18 mg, 0.169 mmol), water (1.1 mL) and iodobenzene (19 μL, 0.17 mmol) were added to a solution of ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (70 mg, 0.16 mmol) in N,N-dimethylformamide (3.4 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (37 mg, 0.032 mmol) was added. The mixture was heated at 100° C. for 3 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10) to afford the desired product ethyl (28g) (42 mg, 0.121 mmol, 75%).

1. customThe solution was degassed under argon
2. temperatureThe mixture was then cooled at room temperature
3. extractionthe aqueous layer was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10)

ORD record

ord-b0fb9884d5d946d3aa859016ef81b95e

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238026B2