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

HRID 249188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249188
[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(N(C(C)C)CC)(C)C.C(OCC)(=O)C>ClCCl.O>[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]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 10617838Ethyl 4-[3-(3-aminobenzoyl)indol-1-yl]butyrateHCID 109353641-Bromohexyl-4-isobutylbenzene

Produkt 1

HCID 19024803Ethyl 4-[3-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]indol-1-yl]butyrateAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-[3-(3-aminobenzoyl)indol-1-yl]butyrate (176 mg), 1-(1-bromohexyl)-4-isobutylbenzene (233 mg) and diisopropylethylamine (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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b9063a40ef664f4f8a451bc39d3e69bb
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212320

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