5-Benzyloxyindole → HCID 19097360, compound

HRID 490753Notes

Reaction equation

HRID 490753 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C.C(OCC)(=O)C>[CH2:25]([O:24][C:22](=[O:23])[CH:21]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)[CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 146245-BenzyloxyindoleHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 19097360HCID 19097360, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of NaH (60%, 4.92 g, 0.205 mol) in DMF (60 mL) is added 5-benzoxyindole at 0˜5° C., then stirred 30 min. ethyl 2-bromopropionate is added dropwise, the mixture is allowed to warm to room temperature and heated at 70° C. overnight, cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate. Concentration and column chromatography on silica gel eluted with hexanes and ethyl acetate yields the title compound (29 g).

Workup

  1. additionis added dropwise
  2. temperatureheated at 70° C. overnight
  3. temperaturecooled to room temperature
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration and column chromatography on silica gel
  7. washeluted with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-cbce632438694c09b41316c1f6143caa
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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