Ethyl Acetate → HCID 22139326, compound

HRID 1749740Notes

Reaction equation

HRID 1749740 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[C:20](OCC)(=[O:22])C>CN(C)C=O>[CH:20]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH:10]=2)[NH:6][CH:7]=1)=[O:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 22139217N-(1H-Indol-5-ylmethyl)acetamide

Product 1

HCID 22139326HCID 22139326, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The synthesis was performed with reference to the known literature (International Patent Publication WO2000/75139). N,N-Dimethylformamide (2.0 mL) cooled to 0° C. was added dropwise with phosphorus oxychloride (0.54 g, 3.5 mmol), and then the mixture was stirred for 15 minutes. Then, the mixture was added with a solution of N-[(1H-indol-5-yl)methyl]acetamide (0.60 g, 3.2 mmol) in N,N-dimethylformamide (4.0 mL), and then the mixture was stirred overnight at room temperature. The reaction mixture was added with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (90:10)) to obtain a solid containing the objective substance. This solid was washed with ethyl acetate to obtain N-[(3-formyl-1H-indol-5-yl)methyl]acetamide (0.12 g, 17%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. washthe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (90:10))
  6. customto obtain a solid
  7. additioncontaining the objective substance
  8. washThis solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-9ff6a28c662242699f2cc6b9b4ffdbc3
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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