Ethyl 7-bromo-1H-indole-2-carboxylate → HCID 68887802, Verbindung

HRID 1760599

Reaktionsgleichung

Reaktionsgleichung von HRID 1760599
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Br:15])=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([CH3:34])OS1(=O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C@H:32]([CH3:34])[CH2:33][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Br:15])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 7017885Ethyl 7-bromo-1H-indole-2-carboxylateHCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 68887802HCID 68887802, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 8.1 g (30.1 mmol) 7-bromo-1H-indole-2-carboxylic acid ethyl ester in 120 ml N,N-dimethylformamide was cooled to 0° C. and 3.55 g (31.6 mmol) potassium tert-butoxide was added. After 30 min., 7.86 g (33.1 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester were added and the cooling bath was removed. After 20 h the reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated. The resulting yellow oil was chromatographed on silica gel (0.032-0.063 mm) with tert-butyl methyl ether: n-hexane (1:8) as eluant to give the desired compound as a yellow oil. ISP-MS: m/e=427.3 ([M+H+]).

Aufarbeitung

  1. customthe cooling bath was removed
  2. additionAfter 20 h the reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting yellow oil was chromatographed on silica gel (0.032-0.063 mm) with tert-butyl methyl ether: n-hexane (1:8) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-1486662615d64122a6df75de1cc7a961
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844345B2

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