Reaction #2328996

Reaction equation

tert-Butyl [5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate

sodium hydride

sodium hydride

1-bromo-2-fluoroethane

1-bromo-2-fluoroethane

→

tert-butyl (2-fluoroethyl)[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONredissolved in EtOAc
3. 3
   workup.ADDITIONWater was added
4. 4
   Otherthe layers separated
5. 5
   ExtractionThe aqueous layer was extracted with EtOAc (2×)
6. 6
   Dryingdried (Na2SO4)
7. 7
   Otherevaporated
8. 8
   Otherto give 253 mg as brown oil
9. 9
   OtherThe crude product was taken to the next step without further purification

Procedure

tert-Butyl [5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]carbamate (0.65 mmol) and sodium hydride (0.78 mmol) were dissolved in dry DMF (20 mL) at 0° C. After 5 min 1-bromo-2-fluoroethane (0.72 mmol) was added and the reaction was allowed to warm to r.t. After 2 h additional sodium hydride and 1-bromo-2-fluoroethane was added and the reaction mixture was stirred over night. The solvent was removed under reduced pressure and redissolved in EtOAc. Water was added and the layers separated. The aqueous layer was extracted with EtOAc (2×), dried (Na2SO4) and evaporated to give 253 mg as brown oil. The crude product was taken to the next step without further purification. MS m/z 388 (M+H).

Source