Benzyl Bromide → HCID 21191857, compound

HRID 2292760Notes

Reaction equation

HRID 2292760 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21].[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(C)=O.O>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10589888HCID 10589888, compound

Product 1

HCID 21191857HCID 21191857, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

5-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide (400 mg, 1.4 mmol) was dissolved in 50 mL of DMSO, 40 mg (1.0 mmol) of 60% NaH/mineral oil added, stirred approximately 0.5 hour, 0.2 mL of benzyl bromide added and stirring maintained 2.5 hours. The mixture was diluted with water, extracted with EtOAc, the EtOAc solution washed with water, saturated NaCl solution, dried (Na2SO4), and concentrated at reduced pressure. The residue was chromatographed on silica (eluted with a gradient, CH2Cl2 →2% MeOH/CH2Cl2) and crystallized from CH2Cl2 /MeOH to give 440 mg (82% yield) of 5-benzyloxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 118°-120° C.

Workup

  1. stirringstirring
  2. temperaturemaintained 2.5 hours
  3. extractionextracted with EtOAc
  4. washthe EtOAc solution washed with water, saturated NaCl solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica (
  8. washeluted with a gradient, CH2Cl2
  9. customcrystallized from CH2Cl2 /MeOH

Sources & evidence

ORD record
ord-6c6b4c8c6aaf425d8a6322d52aa2c4f3
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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