Benzyl Bromide → HCID 86593353, compound

HRID 1071978Notes

Reaction equation

HRID 1071978 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C@@H:3]1[CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:24]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:11][C:2](=[O:1])[C@H:3]1[CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 11172036HCID 11172036, compound

Product 1

HCID 86593353HCID 86593353, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl [(2R)-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetate (Example 1, Step 2, 299 mg, 1.36 mmol) in DMF (5 mL), Cs2CO3 (885 mg, 2.72 mmol) and then (bromomethyl)benzene (0.48 mL, 4.07 mmol) were added. After overnight stirring, the crude reaction mixture was poured into saturated NaHCO3 (50 mL) and extracted with EtOAc (3×50 mL). The combined organics were then washed with water (2×50 mL) and brine (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was subjected to silica gel chromatography eluting with 15%-25% EtOAc in Hexanes to give 131 mg (31%) methyl [(2R)-1-benzyl-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetate. LCMS (ES) 311.3 m/z (M+H)+.

Workup

  1. customthe crude reaction mixture
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organics were then washed with water (2×50 mL) and brine (1×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washeluting with 15%-25% EtOAc in Hexanes

Sources & evidence

ORD record
ord-faab0469b25b4f25b703d2cffee5e7b6
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

Loading…