反応 #48371

反応方程式

NH4Cl

N-(5-fluoropyridin-2-yl)-2,2-dimethylpropanamide

tert-butyllithium

4-dodecylbenzenesulfonyl azide

→

title compound

収率 17.0%

N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide

収率 17.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.WAITAfter 1 h
2. 2
   その他the tetrahydrofuran was removed via rotary evaporator
3. 3
   workup.ADDITIONDichloromethane was added
4. 4
   その他the layers separated
5. 5
   乾燥The combined organics were dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他the residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes

実験手順

To a −78° C. solution of N-(5-fluoropyridin-2-yl)-2,2-dimethylpropanamide (1.34 g, 6.83 mmol) in tetrahydrofuran (25 mL) was added tert-butyllithium (1.31 mL of a 1.7 M solution, 20.5 mmol) drop wise. After 3 h at −78° C., 4-dodecylbenzenesulfonyl azide (3.60 g, 10.2 mmol) was added at the reaction was allowed to warm to room temperature. After 1 h, saturated aqueous NH4Cl was added, and the tetrahydrofuran was removed via rotary evaporator. Dichloromethane was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes, then 5%→42% EtOAc/hexanes) to give the title compound (0.275 g). MS 234.0 (M+1).

出典