Sodium hydride → HCID 69670931, compound

HRID 1191676Notes

Reaction equation

HRID 1191676 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:6]2.[H-].[Na+].Br[CH2:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26].ClCCl.CCCCCC>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26])[C:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[CH:6]2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2928505-methoxy-2-phenyl-1H-indoleHCID 517981Methyl 3-(bromomethyl)benzoateHCID 21226440Methylenechloride Hexane

Product 1

HCID 69670931HCID 69670931, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxy-2-phenylindole (73.0 mg) in N,N-dimethylformamide (1.6 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 22 mg) under cooling with ice, and the mixture was stirred at room temperature for 70 minutes. Then methyl 3-(bromomethyl)benzoate (89.9 mg) was added, and the mixture was stirred at 100° C. for 6 hours. The reaction mixture was cooled to room temperature. Saturated ammonium chloride-water (2/1) were added and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (50.6 mg).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at 100° C. for 6 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionthis resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-35f6fc53193f4e16b940d5b60e832f36
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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