Hydrochloric Acid → HCID 67514581, compound

HRID 1503138Notes

Reaction equation

HRID 1503138 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.C(O[CH2:17][CH3:18])(=O)C.[C:19](=[O:22])([O-])[O-].[Na+].[Na+]>C(OC(=O)C)(=O)C.O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:19](=[O:22])[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 138725-Methoxyindole

Product 1

HCID 67514581HCID 67514581, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-pyridylacetic hydrochloride reduced in powder (2.36 g, 13.6 mmol, 1.0 eq.) in acetic anhydride was heated in a sealed tube at 85° C. for 60 minutes and then, 5-methoxyindole (2 g, 13.6 mmol, 1.0 eq.) was added. The whole was heated at 85° C. for 20 minutes and then, 105° C. for 30 minutes. The reaction was allowed to cool to room temperature and then ethyl acetate and water were added. The pH was adjusted to 7 with saturated aqueous sodium carbonate. The aqueous layer was extracted with ethyl acetate and then, the organic layer was dried over MgSO4. The solvent was removed under reduced pressure and the residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 96/4 to 94/6). The product impure was triturated with ethanol and diethyl ether to afford 1-(5-methoxy-1H-indol-3-yl)-2-pyridin-3-yl-ethanone as a beige powder (1.74 g, 48%).

Workup

  1. temperatureThe whole was heated at 85° C. for 20 minutes
  2. temperatureto cool to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 96/4 to 94/6)
  7. customThe product impure was triturated with ethanol and diethyl ether

Sources & evidence

ORD record
ord-b5a9069bc6ed4f8da6b7b93dcdec597e
Source dataset
uspto-grants-2015_12
Patent number
US09212138B2

Reaction notes

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