Sodium hydride → HCID 117601949, compound

HRID 1773673Notes

Reaction equation

HRID 1773673 reaction equation
[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[H-].[Na+].[C:16]([CH2:20]OS(C(F)(F)F)(=O)=O)([F:19])([F:18])[F:17]>CN(C=O)C>[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[N:7]2[CH2:20][C:16]([F:19])([F:18])[F:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 591410001016316-14-5

Product 1

HCID 117601949HCID 117601949, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-6-methylquinolin-2(1H)-one (103.5 mg, 0.435 mmol) was suspended into DMF (3 mL). To the suspension, was added NaH (17.4 mg 60% in mineral oil) at room temperature. After 2 h stirring, CF3CH2OTf (201.8 mg, 0.869 mmol) was added into the mixture at room temperature. The reaction mixture was stirred for 2 h at the same temperature. The reaction mixture was quenched with water (30 mL). The whole was extracted with AcOEt (30 mL×3). Organic layer was washed with brine (30 mL) and dried over Na2SO4. The solvent was removed under a reduced pressure to give the crude product. Gilson PHPLC purification gave 5-bromo-6-methyl-1-(2,2,2-trifluoroethyl)quinolin-2(1H)-one.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at the same temperature
  2. customThe reaction mixture was quenched with water (30 mL)
  3. extractionThe whole was extracted with AcOEt (30 mL×3)
  4. washOrganic layer was washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under a reduced pressure
  7. customto give the crude product
  8. customGilson PHPLC purification

Sources & evidence

ORD record
ord-ed7478ac64cd45efb6da0ef4734fdb80
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

Loading…