反应详情

温度

-75 °C

N-(5-(trifluoromethyl)pyridin-2-yl)pivalamide (22 g, 89.4 mmole) and TMEDA (33.3 ml, 223.4 mmole) were dissolved in THF (400 ml) under nitrogen and n-BuLi (139.6 ml, 223.4 mmole; 1.6 M solution in n-hexane) was added dropwise at −75° C. The mixture was stirred for 2 hours at −75° C. While maintaining this temperature a solution of iodine (56.7 g, 223.4 mmole) in THF (280 ml) was added dropwise and the reaction mixture was stirred for 2 hours. The reaction mixture was heated to 0° C. and quenched with saturated aqueous sodium thiosulfate solution. The aqueous phase was extracted with DCM (2×150 ml) and the combined organic phases were dried over MgSO4. After filtering off the drying agent and removing the solvent on a rotary evaporator the residue was purified by means of column chromatography (ether: cyclohexane=1:1) and N-(3-iodo-5-(trifluoromethyl)pyridin-2-yl)pivalamide (13 g, 39.1%) was thereby obtained.

1. additionwas added dropwise
2. stirringthe reaction mixture was stirred for 2 hours
3. temperatureThe reaction mixture was heated to 0° C.
4. customquenched with saturated aqueous sodium thiosulfate solution
5. extractionThe aqueous phase was extracted with DCM (2×150 ml)
6. dry with materialthe combined organic phases were dried over MgSO4
7. filtrationAfter filtering off the drying agent
8. customremoving the solvent
9. customon a rotary evaporator the residue
10. customwas purified by means of column chromatography (ether: cyclohexane=1:1) and N-(3-iodo-5-(trifluoromethyl)pyridin-2-yl)pivalamide (13 g, 39.1%)
11. customwas thereby obtained