Water → Ethyl 4-[3-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]indol-1-yl]butyrate

HRID 1034099Notes

Reaction equation

HRID 1034099 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6].Br[CH:28]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(OCC)(=O)C.O>ClCCl>[CH2:40]([C:37]1[CH:36]=[CH:35][C:34]([CH:28]([NH:1][C:2]2[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=2)[C:5]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=2)=[O:6])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:39][CH:38]=1)[CH:41]([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10617838Ethyl 4-[3-(3-aminobenzoyl)indol-1-yl]butyrateHCID 109353641-Bromohexyl-4-isobutylbenzene

Product 1

HCID 19024803Ethyl 4-[3-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]indol-1-yl]butyrateYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 4-[3-(3-aminobenzoyl)indol-1-yl]-butyrate (176 mg), 1-(1-bromohexyl)-4-isobutylbenzene (233 mg) and diisopropytethylamine (194 mg) in dichloromethane (5 ml) was refluxed for 20 hours. The reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was separated and washed-with water and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel column eluting with a mixture of n-hexane-and ethyl acetate (3:1) to give ethyl 4-[3-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]-indol-1-yl]butyrate (155 mg) as an oil.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customThe organic layer was separated and washed-with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel column
  6. washeluting with a mixture of n-hexane-and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ad641ed428304790a5c8ce3a230f85c4
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

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