Dimethylformamide → HCID 18473977, compound

HRID 2227526Notes

Reaction equation

HRID 2227526 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[O:4][CH:5]([CH:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[OH:20])[NH:13][CH:12]=2)[CH3:10])[C:6](=[O:8])[N:7]=1.[CH3:22]N(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:21][N:2]([CH3:1])[C:3]1[O:4][CH:5]([CH:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][CH3:22])[NH:13][CH:12]=2)[CH3:10])[C:6](=[O:8])[N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 184739322-(Dimethylamino)-5-[1-(4-hydroxy-1H-indol-3-yl)ethyl]-4(5H)-oxazolone

Product 1

HCID 18473977HCID 18473977, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-dimethylamino-5-[1-(4-hydroxyindol-3-yl)ethyl]2-oxazolin-4-one (120 mg) was dissolved into dimethylformamide (3 ml). Potassium carbonate (115 mg) and indomethane (156 l) were added. The mixture was stirred for 3 hours at room temperature and additional indomethane (78 μl) was added. The mixture was stirred for 36 hours at room temperature. To the reaction mixture was added water and the whole was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Concentration of the ethyl acetate solution gave a residue, which was subjected to silica gel chromatography. Elution with hexane-acetone (1:1) provided 2-dimethylamino-5-[1-(4-methoxyindol-3-yl)ethyl]-2-oxazolin-4-one (54 mg).

Workup

  1. additionadditional indomethane (78 μl) was added
  2. stirringThe mixture was stirred for 36 hours at room temperature
  3. extractionthe whole was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customConcentration of the ethyl acetate solution gave a residue, which
  7. washElution with hexane-acetone (1:1)

Sources & evidence

ORD record
ord-b9ed3d3e990f4a74a154a8ba0401746e
Source dataset
uspto-grants-2002_07
Patent number
US06414003B1

Reaction notes

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