Potassium Carbonate → 6-Bromo-2a-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-yl)-butyl]-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

HRID 2301076Notes

Reaction equation

HRID 2301076 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(=O)([O-])[O-].[K+].[K+].[Br:20][C:21]1[CH:29]=[CH:28][C:27]2[NH:26][C:25](=[O:30])[C:24]3([CH2:34][CH2:35][CH2:36][CH2:37]Br)[CH2:31][CH2:32][CH2:33][C:22]=1[C:23]=23>CN(C=O)C>[Br:20][C:21]1[CH:29]=[CH:28][C:27]2[NH:26][C:25](=[O:30])[C:24]3([CH2:34][CH2:35][CH2:36][CH2:37][N:2]4[CH2:3][CH2:4][C:5]5[C:13]6[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=6)[NH:7][C:6]=5[CH2:1]4)[CH2:31][CH2:32][CH2:33][C:22]=1[C:23]=23

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107838Tetrahydro-beta-carbolineHCID 109819466-Bromo-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 183773546-Bromo-2a-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-yl)-butyl]-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 31 mg (0.18 mmol) portion of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and 62 mg (0.54 mmol) of potassium carbonate were added to 1 ml of DMF solution containing 58 mg (0.15 mmol) of 6-bromo-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 residue was recrystallized from acetone-diisopropyl ether to obtain 50 mg of the title compound (70% 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 residue was recrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-5601c5bb63af4f0c9829a0fd45803501
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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