Ethyl Acetate → HCID 67141782, compound

HRID 1445092Notes

Reaction equation

HRID 1445092 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 matertals. The reaction mixture 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 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-717694e1bc0a4bdf90d513623bc9d414
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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