1-Pentene → HCID 67726848, compound

HRID 1938164Notes

Reaction equation

HRID 1938164 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:28])[NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:14]=1)[C:7](=[O:29])[N:6]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:5]2=[O:36].C(=O)([O-])[O-].[K+].[K+].[CH2:43]=[CH:44][CH2:45][CH2:46][CH3:47]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:43]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:28])[NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:14]=1)[C:7](=[O:29])[N:6]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:5]2=[O:36])=[CH:44][CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 3

HCID 80041-PenteneHCID 11430Potassium CarbonateHCID 21469076HCID 21469076, compound

Product 1

HCID 67726848HCID 67726848, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

1.09 g (1.8 mmol) of 6-iodo-3-(2-methoxycarbonylethyl)-1-(N-t-butylcarbamoyl-3-indolylmethyl)quinazoline-2,4-dione and 0.75 g (5.4 mmol) of potassium carbonate were introduced in 15 ml of DMF, and 0.63 g (9.0 mmol) of 1-pentene, 0.58 g (1.8 mmol) of tetrabutylammonium bromide and 10 mg of palladium acetate were added. The mixture was stirred at room temperature for 48 h and then concentrated under reduced pressure. The crude product was chromatographed on silica gel, eluent dichloromethane (2% methanol). 0.69 g (70%) of product, RF 0.12 (dichloromethane+2% methanol) was obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was chromatographed on silica gel, eluent dichloromethane (2% methanol)

Sources & evidence

ORD record
ord-0f2f35cb3e5043afa0441e22357d1686
Source dataset
uspto-grants-1997_12
Patent number
US05693637

Reaction notes

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