Sodium hydride → HCID 69671126, compound

HRID 1191678Notes

Reaction equation

HRID 1191678 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]=[CH:24][C:25]([F:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28].[Cl-].[NH4+]>CN(C)C=O>[F:32][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2928505-methoxy-2-phenyl-1H-indoleHCID 22645461Methyl 5-(bromomethyl)-2-fluorobenzoate

Product 1

HCID 69671126HCID 69671126, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxy-2-phenylindole (90.9 mg) in N,N-dimethylformamide (1.8 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 18 mg) under cooling with ice and an argon atmosphere, and the mixture was stirred under cooling with ice for 5 minutes and then at room temperature for 15 minutes. Methyl 5-(bromomethyl)-2-fluorobenzoate (101 mg) was added at room temperature, and the mixture was stirred at 80° C. for 13 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (53.2 mg).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 5 minutes
  3. stirringthe mixture was stirred at 80° C. for 13 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cef8df29803342a882eaccc5f00eb95f
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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