2-Fluoroethyl bromide → HCID 59203840, compound

HRID 2241814Notes

Reaction equation

HRID 2241814 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14][CH:15]=3)[O:9][C:5]=2[CH:4]=1.[H-].[Na+].Br[CH2:29][CH2:30][F:31]>CN(C=O)C>[F:31][CH2:30][CH2:29][N:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:25]=[CH:24][C:6]=3[N:7]=2)=[CH:15][N:14]=1)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 129822-Fluoroethyl bromide2×HCID 24758Sodium hydride2×HCID 24780959HCID 24780959, compound

Product 1

HCID 59203840HCID 59203840, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionredissolved in EtOAc
  3. additionWater was added
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give 253 mg as brown oil
  9. customThe crude product was taken to the next step without further purification

Sources & evidence

ORD record
ord-2b6273ec99a24216aaa92b72ab208139
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

Loading…