Sodium Bicarbonate → HCID 22316823, compound

To a stirred solution of 2-methyl-5-[4-(methylsulfonyl)phenyl]-4-(4-bromophenyl)-oxazole (0.314 g, 0.8 mmol) in DME (10 mL) was added thiophene-2-boronic acid (0.123 g, 0.96 mmol), bis(triphenylphosphine)palladium(II)chloride (0.064 g, 0.09 mmol) and saturated NaHCO3 solution (3.2 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 4.5 hours, and cooled down to room temperature. The reaction mixture was filtered through celite, the filtrate was poured into water and the whole was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (3/2). The resulting solid was recrystallized from ethyl acetate/hexane to give the title compound (0.225 g, 71.2% yield).

1. temperatureThe mixture was heated
2. temperatureat reflux temperature for 4.5 hours
3. filtrationThe reaction mixture was filtered through celite
4. additionthe filtrate was poured into water
5. extractionthe whole was extracted with ethyl acetate (10 mL×3)
6. washThe organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash chromatography
10. washeluting with hexane/ethyl acetate (3/2)
11. customThe resulting solid was recrystallized from ethyl acetate/hexane

ORD record

ord-047a4a69826f480ba9618d6d2ce584bf

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949536B2