Ethyl Acetate → HCID 67141782, compound

HRID 1932378Notes

Reaction equation

HRID 1932378 reaction equation
[Cu][C:2]#[N:3].Cl[C:5]1[CH:6]=[C:7]2[C:23]([CH3:24])=[C:22]([CH3:25])[NH:21][C:8]2=[C:9]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)[N:10]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][CH2:20][N:11]1[C:9]1[N:10]=[C:5]([C:2]#[N:3])[CH:6]=[C:7]2[C:23]([CH3:24])=[C:22]([CH3:25])[NH:21][C:8]=12

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 86615261HCID 86615261, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67141782HCID 67141782, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Copper(I) cyanide (9.3 g, 102.6 mmol) was added to a solution of 2-(5-chloro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline (3.2 g, 10.3 mmol) prepared in Example 656 in anhydrous N,N-dimethylformamide (100 ml). The reaction mixture was refluxed for 24 hours and then cooled to room temperature. Ethyl acetate was added to the reaction mixture, which was then filtered to discard insoluble materials. The reaction mixture was washed with water. 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=1/3, v/v) to give 750 mg of the titled compound as a white solid. (Yield: 26%)

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. filtrationwas then filtered
  3. washThe reaction mixture was washed with water
  4. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Sources & evidence

ORD record
ord-62476a18b936402a86e3b14a370d69b1
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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