Cesium carbonate → N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide

温度

100 °C

1-(3,5-Dichloro-pyrazin-2-yl)-ethanone (200 mg) and 2,3-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (448.3 mg), prepared as in example 1, was added to a reaction vessel containing a magnetic stirring bar together with 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (61 mg) and cesium carbonate (1.0 g), followed by 9 ml dioxane and 1 ml water, and the mixture heated to 100° C. under stirring. After 2 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (30 ml) and extracted with EtOAc (3×30 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil-Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide as a colorless solid after evaporation of the solvents under reduced pressure. Yield: 230 mg (48%).

1. additionwas added to a reaction vessel
2. temperatureAfter 2 h the reaction mixture was cooled to RT
3. customquenched with a saturated aqueous sodium bicarbonate solution (30 ml)
4. extractionextracted with EtOAc (3×30 ml)
5. dry with materialThe combined organic phases were dried over sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customto afford the crude product as a brown oil-Purification by flash chromatography on silica gel using

ORDレコード

ord-31b0825a0a5343a99cfedda808ab3ea2

出典データセット

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09174993B2