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Ethyl bromoacetate → tert-Butyl[1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetate

HRID 551041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 551041
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:6]1[C:7]2[C:12](=[C:11]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]=[CH:9][CH:8]=2)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5]1)[CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 57426200tert-Butyl [3-nitro-1H-indol-4-yl]acetate

Produkt 1

HCID 57426201tert-Butyl[1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl [3-nitro-1H-indol-4-yl]acetate from Step D (385 mg, 1.39 mmol) in DMF (5 mL) at ambient temperature was added sodium hydride (60 mg of a 60% dispersion in mineral oil, 1.50 mmol). The reaction mixture was stirred for 5 min, then ethyl bromoacetate (256 mg, 1.53 mmol) was added and stirring was continued for 10 min. The reaction was quenched with saturated aqueous NaHCO3 (5 mL) and extracted with CHCl3 (2×25 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 40:60, to give the title compound. MS: m/z=307 (M−C4H7).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 10 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3 (5 mL)
  4. extractionextracted with CHCl3 (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-f0012ebcaa61441b8848430e10e891fd
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947677B2

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