تفاعل #48371

معادلة التفاعل

NH4Cl

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

tert-butyllithium

4-dodecylbenzenesulfonyl azide

→

title compound

المردود 17.0%

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

المردود 17.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 1 h
2. 2
   أخرىthe tetrahydrofuran was removed via rotary evaporator
3. 3
   workup.ADDITIONDichloromethane was added
4. 4
   أخرىthe layers separated
5. 5
   تجفيفThe combined organics were dried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىthe residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes

الإجراء التجريبي

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).

المصدر