Pinoline → 2a-[4-(6-Methoxy-2,3,4,9-tetrahydro-1H-prido[3,4-b]indol-2-yl)-butyl]-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

HRID 2301074Notes

Reaction equation

HRID 2301074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH2:12][NH:13][CH2:14][CH2:15][C:6]2=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]12[CH2:38][CH2:37][CH2:36][C:34]3[C:35]1=[C:30]([CH:31]=[CH:32][CH:33]=3)[NH:29][C:28]2=[O:39]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH2:12][N:13]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]34[CH2:38][CH2:37][CH2:36][C:34]5[C:35]3=[C:30]([CH:31]=[CH:32][CH:33]=5)[NH:29][C:28]4=[O:39])[CH2:14][CH2:15][C:6]2=1

Participants

5

Reactant 3

HCID 1868PinolineHCID 11430Potassium CarbonateHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 111020492a-[4-(6-Methoxy-2,3,4,9-tetrahydro-1H-prido[3,4-b]indol-2-yl)-butyl]-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 295 mg (1.46 mmol) portion of 6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and 404 mg (2.91 mmol) of potassium carbonate were added to 7 ml of DMF solution containing 300 mg (0.97 mmol) of 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the thus obtained oil was purified by a silica gel column chromatography (80 cc; elution by chloroform-methanol=15:1) and recrystallized from acetone-diisopropyl ether to obtain 369 mg of the title compound (88% in yield).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe thus obtained oil was purified by a silica gel column chromatography (80 cc; elution by chloroform-methanol=15:1)
  6. customrecrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-64c4edb03d8b4d6c97e9a51dba1d7926
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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