Cesium fluoride → Tert-butyl 3-(4-(methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-ylcarbamate

温度

80 °C

To a mixture of tert-butyl 3-bromo-1,2,4-thiadiazol-5-ylcarbamate (1.90 g, 6.78 mmol), 4-(methylsulfonyl)phenylboronic acid (2.07 g, 10.3 mmol), cesium fluoride (2.09 g, 13.8 mmol), and the palladium catalyst (0.271 g, 0.383 mmol) was added dioxane (20 mL) and water (2 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 min and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was diluted with EtOAc, and the organic phase was washed with saturated NH4Cl (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in hexanes) gave tert-butyl 3-(4-(methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-ylcarbamate.

1. customThe reaction mixture was degassed
2. customby bubbling nitrogen through the solution for 5 min
3. additionThe reaction mixture was diluted with EtOAc
4. washthe organic phase was washed with saturated NH4Cl (1×), brine (1×)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in hexanes)

ORDレコード

ord-5eeca1c9b6e1420caeeeb9e33f8e424e

出典データセット

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08324396B2