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Ethyl 1H-indole-3-acetate → tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

HRID 1471628
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1471628
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:2]1.[Br:16]N1C(=O)CCC1=O.[C:24]([O:31]C(OC(C)(C)C)=O)(=O)[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:16][C:2]1[N:1]([C:24]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:31])[C:9]2[C:4]([C:3]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:6]=[CH:7][CH:8]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 13067Ethyl 1H-indole-3-acetateHCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

Produkt 1

HCID 90281421tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylateAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-(1H-indol-3-yl)acetate (5 g, 24.6 mmol) in 25 ml of DCM was added N-bromosuccinimide (4.38 g, 24.6 mmol) in small portions at 0° C. The mixture was warmed to room temperature and stirred for 6 hours. Di-tert-butyl pyrocarbonate (10.74 g, 49.2 mmol), DIPEA (8.6 ml, 49.5 mmol) and DMAP (cat) was added to the mixture. The reaction was stirred overnight. The mixture was diluted with DCM (100 ml) and washed with HCl (0.5 N, 2×50 ml). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography on silica (5-20 EtOAc/hexanes) to get 6.3 g (16.5 mmol) of product. MS (m/z) 382 [M+H]+.

Aufarbeitung

  1. stirringThe reaction was stirred overnight
  2. washwashed with HCl (0.5 N, 2×50 ml)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe crude product was introduced to a silica gel loading column
  7. custompurified by column chromatography on silica (5-20 EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1e14f1328bbf4979b2146d42f154a45f
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012441B2

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