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Methanol → Ethyl 3-chloro-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate

HRID 1875034
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1875034
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]([O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2)=[O:15])([CH3:12])[CH3:11].CO>ClCCl>[Cl:1][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:14]([O:13][C:10]([CH3:9])([CH3:11])[CH3:12])=[O:15])[CH:18]=2)[NH:22][C:21]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 31398ChlorosuccinimideHCID 22105416Ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate

Produkt 1

HCID 68485443Ethyl 3-chloro-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

N-Chlorosuccinimide (0.044 g, 0.329 mmol) to a suspension of ethyl 5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.100 g, 0.329 mmol) in dichloromethane (5 mL). Methanol (2 mL) was added to complete solution. The mixture was stirred at room temperature overnight. The solvent was evaporated, the residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (0.082 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.93 (s, 1H), 9.31 (br. s., 1H), 7.80 (br. s., 1H), 7.28-7.32 (m, 2H), 4.31 (q, 2H), 1.44 (s, 9H), 1.25-1.35 (m, 3H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-115c467d09af4deb92eaa54f19f3c240
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304419B2

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