Ethyl Acetate → HCID 18377409, compound

HRID 2301112Notes

Reaction equation

HRID 2301112 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].C(=O)([O-])[O-].[K+].[K+].[C:25]([O:28][CH2:29][CH3:30])(=O)[CH3:26]>CN(C)C=O>[O:28]1[C:25]2[CH2:26][CH2:9][N:8]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]34[CH2:17][CH2:16][CH2:15][C:13]5[C:14]3=[C:9]([CH:10]=[CH:11][CH:12]=5)[NH:8][C:7]4=[O:18])[CH2:7][C:6]=2[CH:30]=[CH:29]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 18377409HCID 18377409, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine (410 mg, 1.9 mmol) was dissolved in ethanol (4 ml), and the solution was mixed with 10% palladium on activated carbon (80 mg) and stirred at room temperature for 15 hours in an atmosphere of hydrogen. The reaction solution was filtered to remove 10% palladium on activated carbon, and the solvent was removed by evaporation under a reduced pressure to obtain crude 4,5,6,7-tetrahydro-furo[3,2-c]pyridine. This compound and 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (590 mg, 1.9 mmol) and potassium carbonate (400 mg, 2.9 mmol) were stirred at room temperature for 18 hours in anhydrous N,N-dimethylformamide (4 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 94 mg (0.27 mmol, 14% in yield) of the title compound.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was removed by evaporation from the organic layer under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-a9352f1d8d264e1e8b19e3b9b73e2cdf
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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