Potassium Hydroxide → HCID 67142301, compound

HRID 1445096Notes

Reaction equation

HRID 1445096 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([N:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[N:14]=[C:15]([C:17]#[N:18])[CH:16]=[C:11]2[C:10]([CH3:29])=[C:9]1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:31].[K+]>C(O)C.O>[CH2:1]([N:8]1[C:12]2=[C:13]([N:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[N:14]=[C:15]([C:17]([NH2:18])=[O:31])[CH:16]=[C:11]2[C:10]([CH3:29])=[C:9]1[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67142062HCID 67142062, compound

Product 1

HCID 67142301HCID 67142301, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1-Benzyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 0.76 mmol) prepared in Example 686 was diluted with a mixture of ethanol (7 ml) and water (1 ml). Potassium hydroxide (426 mg, 7.6 mmol) was added to the solution, which was then refluxed for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v) to give 260 mg of the titled compound as a white solid. (Yield: 84%)

Workup

  1. temperaturewas then refluxed for 2 hours
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1

Sources & evidence

ORD record
ord-e94f2c81bce04124a75aedb9f96bde66
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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