反应详情

温度

100 °C

1-(4-Chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(5-bromo-pyridin-3-yl)-butyl]-amide (100 mg, 0.22 mmol), copper(II) triflate (81 mg, 0.22 mmol), sodium methylsulfinate (80 mg, 0.67 mmol) are added to a reaction vial with a septum top which is then evacuated and filled with nitrogen for 3 cycles. DMSO (1 mL) and N,N′-dimethylethylenediamine (71 μL, 0.67 mmol) are added and the reaction is heated at 100° C. for 30 hours. The resultant mixture is cooled to room temperature, diluted with EtOAc (50 mL), and washed with saturated aqueous ammonium chloride (2×25 mL), saturated aqueous sodium bicarbonate (25 mL) and brine (25 mL). The combined organic layers are dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material is purified by preparative reverse phase HPLC (eluted with 10 to 95% CH3CN/H2O and 0.1% TFA as additive) to afford 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(5-methanesulfonyl-pyridin-3-yl)-butyl]-amide as a colorless foam (30 mg, 30%).

1. customis then evacuated
2. additionfilled with nitrogen for 3 cycles
3. washwashed with saturated aqueous ammonium chloride (2×25 mL), saturated aqueous sodium bicarbonate (25 mL) and brine (25 mL)
4. dry with materialThe combined organic layers are dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude material is purified by preparative reverse phase HPLC (eluted with 10 to 95% CH3CN/H2O and 0.1% TFA as additive)