Dichloromethane → Methyl 4-(2,4-difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

온도

80 °C

To a suspension of methyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-thiazole-5-carboxylate (100 mg, 0.237 mmol) obtained in Example 13-B (ii), 2,4-difluorophenylboronic acid (56.2 mg, 0.356 mmol), and cesium carbonate (154 mg, 0.474 mmol) in DME (5 mL) and water (1 mL) under argon atmosphere was added [1,1′-B is(diphenylphosphino)ferrocene]palladium(II) dichloride complex with dichloromethane (1:1) (19.4 mg, 0.0237 mmol) and the mixture was stirred for 80° C. To the mixture were added EtOAc (20 mL) and saturated aqueous solution of sodium bicarbonate (15 mL) and then organic layer was separated. The aqueous layer was extracted with EtOAc (5 mL) and the combined organic layer was washed with brine (5 mL). The organic layer was separated and then filtered through silica gel pad (3 g). After the concentration of the filtrate, the residue was washed with EtOAc (2 mL) to obtain title compound (79 mg, 87%) as a colorless solid.

1. customorganic layer was separated
2. extractionThe aqueous layer was extracted with EtOAc (5 mL)
3. washthe combined organic layer was washed with brine (5 mL)
4. customThe organic layer was separated
5. filtrationfiltered through silica gel pad (3 g)
6. washAfter the concentration of the filtrate, the residue was washed with EtOAc (2 mL)

ORD 기록

ord-998f66e555654077a5ceeb90131a3cbd

출처 데이터셋

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09090601B2