反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 82 °C
PROCEDURE
实验过程
Argon was bubbled through 5-iodo-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (SM2, 200 mg, 0.46 mmol) and [1-(4-cyanophenyl)-1H-pyrazol-5-yl]boronic acid (SM3, 150 mg, 0.70 mmol) in DME (10 ml) and 2M Na2CO3 (5 ml) for 10 min. Palladium-tri-tert-butylphosphine (25 mg, 0.049 mmol) was added and the mixture was stirred under argon at 82° C. for 2 h. More SM3 (150 mg, 0.70 mmol) and palladium-tri-tert-butylphosphine (10 mg, 0.019 mmol) were added and the mixture was stirred for a further 2 h under the same conditions. The reaction mixture was then was cooled to RT, diluted with ethyl acetate (150 ml) and washed with brine (3×100 ml). The organic phase was dried (Na2SO4), filtered and evaporated. The residue was purified by HPLC on a Kromasil C-18 column using a gradient of acetonitrile/water. Freeze-drying of the mixture afforded the title compound (80 mg).
WORKUP
后处理
- stirringthe mixture was stirred for a further 2 h under the same conditions
- temperatureThe reaction mixture was then was cooled to RT
- washwashed with brine (3×100 ml)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe residue was purified by HPLC on a Kromasil C-18 column
- customFreeze-drying of the mixture