Triethylamine → Methyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate

HRID 453856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453856
Br[CH2:2][C:3]1[N:4]([CH3:17])[C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[CH:8]=[CH:7][CH:6]=2.[NH2:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[CH:24][N:25]2[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:21][CH:20]=1.C(N(CC)CC)C>C1C=CC=CC=1.C(OCC)(=O)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([NH:18][CH2:2][C:3]3[N:4]([CH3:17])[C:5]4[C:10]([C:11]=3[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[CH:8]=[CH:7][CH:6]=4)[CH:27]=2)[CH:23]=[CH:24]1)([CH3:35])([CH3:33])[CH3:34]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 59473728tert-butyl 2-(6-amino-1H-indol-1-yl)acetate2×HCID 59473756Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate

Produkt 1

HCID 68427131Methyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-4-chloro-1-methyl-1H-indole-3-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate (1.10 mmol, 1.0 equiv.) and tert-butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A) (1.10 mmol, 1.0 equiv.) were dissolved in benzene (5 ml) and triethylamine (1.3 mmol, 1.2 equiv.) and refluxed for 16 h. The reaction mixture was cooled to 25° C., diluted with ethyl acetate and washed with water and sat. NaCl solution. Drying over Na2SO4 was then carried out, followed by concentration under reduced pressure. The crude product was purified by column chromatography (40% ethyl acetate in hexane). Yield: 55%

Aufarbeitung

  1. washwashed with water and sat. NaCl solution
  2. dry with materialDrying over Na2SO4
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe crude product was purified by column chromatography (40% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f1c1fff7fd3743aebba8912a66a5d9a6
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492559B2

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