Sodium hydride → HCID 69671081, compound

HRID 1191684Notes

Reaction equation

HRID 1191684 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+].Cl[CH2:21][C:22]1[O:23][CH:24]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=1.[Cl-].[NH4+]>CN(C)C=O.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[O:23][CH:24]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=1)[C:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[CH:6]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2928505-methoxy-2-phenyl-1H-indoleHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylate

Product 1

HCID 69671081HCID 69671081, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methoxy-2-phenylindole (205 mg) in N,N-dimethylformamide (4.6 mL) was added sodium hydride (in oil, 50 to 72%, 55 mg) under cooling with ice and an argon atmosphere, and the mixture was stirred at room temperature for 2 hours. Then methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (193 mg) was added, and the mixture was stirred at 80° C. for 22 hours. The reaction mixture was allowed to cool to ambient temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (229 mg).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at 80° C. for 22 hours
  3. temperatureto cool to ambient temperature
  4. extractionthis resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively 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 (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-489ea51b07384096b815d1bd64fc293f
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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