Hydrochloric Acid → HCID 58378243, compound

HRID 241611Notes

Reaction equation

HRID 241611 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]#[N:18])=[C:9]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[OH:25]O.[OH-].[K+].Cl>CO.CCOC(C)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]([NH2:18])=[O:25])=[C:9]2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 44463000HCID 44463000, compound

Product 1

HCID 58378243HCID 58378243, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Hydroxy-phenyl)-2-phenyl-1H-indole-3-carbonitrile (Example 46, 10 mg, 0.03 mmol) was dissolved in 1 ml of MeOH. H2O2 (1 ml, 35% by weight in H2O) and 2M KOH (0.5 ml) were added and the reaction mixture was heated to reflux over night. The mixture was acidified with 1M HCl and EtOAc was added. The phases were separated and the organic solvents were evaporated. The crude product was purified by reversed phase preparative HPLC to give the title amide. ES/MS m/z: 329.1 (M+H), 327.13 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.34 (m, 1H), 7.46 (m, 2H), 7.40-7.37 (m, 3H), 7.24-7.18 (m, 2H), 7.12 (m, 2H), 7.07 (m, 1H) and 6.85 (m, 2H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux over night
  3. additionwas added
  4. customThe phases were separated
  5. customthe organic solvents were evaporated
  6. customThe crude product was purified by reversed phase preparative HPLC

Sources & evidence

ORD record
ord-8705ed5bf1f7472dbd10f9faf394b3d9
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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