Benzyl Bromide → HCID 57015605, compound

HRID 1417482Notes

Reaction equation

HRID 1417482 reaction equation
[S:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:14][C:15]1[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.O>[CH2:24]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]2[CH2:4][CH2:3][CH:2]([CH2:14][C:15]3[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=3)[S:1][C:6]1=2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 543591052-(2,3,4,9-Tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazoline

Product 1

HCID 57015605HCID 57015605, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

71 mg of 2-(2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazoline (prepared as described in Example 80) in 1 ml of dimethylformamide was added to a suspension of 11 mg of sodium hydride (55% w/w dispersion in mineral oil) in 1 ml of dimethylformamide, with stirring and ice-cooling. Stirring was continued at this temperature for 30 minutes and then 0.03 ml of benzyl bromide was added to the reaction mixture, with stirring and ice-cooling. Stirring was continued for a further hour. At the end of this time, the reaction mixture was diluted with water and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography, using a mixture of 20% v/v ethyl acetate in hexane as the eluent, to afford 71 mg of the title compound as an oil.

Workup

  1. temperatureice-cooling
  2. stirringStirring
  3. stirringwith stirring
  4. temperatureice-cooling
  5. stirringStirring
  6. waitwas continued for a further hour
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate fraction was then washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was then removed by evaporation under reduced pressure
  11. customthe resulting residue was purified by silica gel column chromatography
  12. additiona mixture of 20% v/v ethyl acetate in hexane as the eluent

Sources & evidence

ORD record
ord-5dc7efb2110a4dc2a4b6fa6ebbe6137e
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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