Réaction #48371

Équation de réaction

NH4Cl

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

tert-butyllithium

4-dodecylbenzenesulfonyl azide

→

title compound

Rendement 17.0%

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

Rendement 17.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source