Allyl bromide → HCID 15678802, compound

HRID 1090202Notes

Reaction equation

HRID 1090202 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH:32]=[CH2:33]>CC(C)=O.O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:33][CH:32]=[CH2:31])=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 156787821-[(4-Chlorophenyl)methyl]-5-hydroxy-3-methyl-1H-indole-2-propanoic acid

Product 1

HCID 15678802HCID 15678802, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Using 845 mg of the product of Example 23 as starting material, diluted in 23 ml of dimethyl ketone, 476 mg of potassium carbonate and 225 μl of allyl bromine was added. The reaction was refluxed overnight. The reaction was then diluted with water and the acetone removed in vacuo. Then the reaction was extracted with CH3CO2Et and the organic phase was dried and concentrated to yield after flash chromatography (hexane 8, ethyl acetate 2) 790 mg of the compound, which was then hydrolyzed following the procedure of Example 2.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customthe acetone removed in vacuo
  3. extractionThen the reaction was extracted with CH3CO2Et
  4. customthe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-923aaa4b0f2c45738394d853fb25f016
Source dataset
uspto-grants-1992_01
Patent number
US05081145

Reaction notes

Loading…