Water → HCID 18973514, compound

HRID 2394396Notes

Reaction equation

HRID 2394396 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Cl[CH2:17][C:18]1[N:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:21][C:22]=1[CH3:23].O>CN(C)C=O>[CH3:23][C:22]1[O:21][C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:19][C:18]=1[CH2:17][N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2733668methyl 1H-indole-4-carboxylateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 18973514HCID 18973514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl indole-4-carboxylate (700 mg) was dissolved in 7 ml of dimethylformamide, then 160 mg of sodium hydride (content 60%) was added to the resulting solution at room temperature and the mixture was stirred for 30 minutes. After adding 830 mg of 4-chloromethyl-5-methyl-2-phenyloxazole to the mixture and stirring them for 2 hours, the reaction solution was added to 70 ml of water and extracted with ethyl acetate (50 ml×2). The resulting organic phase was washed with, in order, water (50 ml×2) and 50 ml of a saturated common salt aqueous solution and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the residue was crystallized in 50 ml of hexane to thus give 1.18 g of methyl 1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole-4-carboxylate as pale brown crystals. The yield thereof was found to be 85%.

Workup

  1. stirringstirring them for 2 hours
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. washThe resulting organic phase was washed with, in order, water (50 ml×2) and 50 ml of a saturated common salt aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe residue was crystallized in 50 ml of hexane to thus give 1.18 g of methyl 1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole-4-carboxylate as pale brown crystals
  7. customThe yield

Sources & evidence

ORD record
ord-76ed2849529747c6b115a993ca73e88b
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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