Hydrochloric Acid → HCID 58378243, compound

HRID 383450Notes

Reaction equation

HRID 383450 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-3aeeb2fc158543118e052aebf67c9508
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

Loading…