Hydrochloric Acid → HCID 19024710, compound

HRID 249170Notes

Reaction equation

HRID 249170 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH:37]([CH3:39])[CH3:38])=[CH:32][CH:31]=2)[CH2:12][C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:17])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].Br[CH2:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:30]2[CH:31]=[CH:32][C:33]([CH2:36][CH:37]([CH3:39])[CH3:38])=[CH:34][CH:35]=2)[CH2:12][C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH:19]=2)=[O:17])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 76300Ethyl 4-bromobutyrate2×HCID 19024734HCID 19024734, compound

Product 1

HCID 19024710HCID 19024710, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3-[3-[2,2-bis(4-isobutylphenyl)ethyl]benzoyl]indole (442 mg), ethyl 4-bromobutyrate (185 mg) and potassium carbonate (360 mg) in N,N-dimethylformamide (10 ml) was stirred at 20° C. for 4 hours. Ethyl 4-bromobutyrate (185 mg) and potassium carbonate (120 mg) were added, and resulting mixture was stirred at 20° C. for 16 hours. The reaction mixture was poured into a mixture of ethyl acetate and 1N-hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (20 g) eluting with a mixture of hexane and ethyl acetate (10:1) to give ethyl 4-[3-[3-[2,2-bis(4isobutylphenyl)ethyl]benzoyl]indol-1-yl]butyrate (480 mg) as an oil.

Workup

  1. customresulting mixture
  2. stirringwas stirred at 20° C. for 16 hours
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by column chromatography on silica gel (20 g)
  8. washeluting with a mixture of hexane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-e96fca8fb4a6487c98e3e5341b7d3bbf
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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