Potassium Carbonate → Ethyl 2-methyl-8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate

온도

120 °C

A mixture of ethyl 8-chloro-2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate (380 mg), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(triisopropylsilyl)oxazole (479 mg), tetrakis(triphenylphosphine)palladium(0) (143 mg) and potassium carbonate (343 mg) in DME/water (8/2 mL) was stirred with microwave irradiation at 120° C. for 30 min. The reaction mixture was diluted with water, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in THF (12 mL), and 1N hydrochloric acid (4 mL) was added thereto. The reaction mixture was stirred at room temperature for 2 hr, saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (78 mg).

1. extractionextracted with ethyl acetate
2. dry with materialThe extract was dried over anhydrous magnesium sulfate
3. customthe solvent was evaporated under reduced pressure
4. dissolutionThe residue was dissolved in THF (12 mL)
5. addition1N hydrochloric acid (4 mL) was added
6. stirringThe reaction mixture was stirred at room temperature for 2 hr
7. additionsaturated aqueous sodium bicarbonate solution was added
8. extractionthe mixture was extracted with ethyl acetate
9. dry with materialThe extract was dried over anhydrous magnesium sulfate
10. customthe solvent was evaporated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
12. customthe obtained solid was recrystallized from ethyl acetate/hexane

ORD 기록

ord-ed6b6ec351ba448499758efd73aeb463

출처 데이터셋

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09296746B2