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Sodium hydride → HCID 11713695, Verbindung

HRID 1880466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1880466
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13]3[NH:14][C:15]4[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=4[C:21]=3[O:22][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:31][C:32]1[CH:45]=[CH:44][C:35]([O:36][CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:34][CH:33]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13]3[N:14]([CH2:31][C:32]4[CH:45]=[CH:44][C:35]([O:36][CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:34][CH:33]=4)[C:15]4[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=4[C:21]=3[O:22][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 11515692HCID 11515692, VerbindungHCID 124936922-[4-(Chloromethyl)phenoxy]-N,N-diethylethan-1-amine--hydrogen chloride (1/1)

Produkt 1

HCID 11713695HCID 11713695, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 7-benzyloxy-3-methoxy-10H-benzo[4,5]furo[3,2-b]indole (102 mg, 0.297 mmol) in DMF (5 mL) was added NaH (37 mg, 60% in mineral oil, 3.0 eq.) followed by [2-(4-chloromethyl-phenoxy)-ethyl]-diethyl-amine hydrochloride salt (99 mg, 0.356 mmol) at 0° C. The mixture was stirred at 0° C. for 30 minutes, warmed to 25° C., and quenched by NH4Cl (solid). EtOAc and water were then added to the mixture. The reaction mixture was then partitioned between EtOAc and water. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield crude material. The crude material was purified by silica gel (EtOAc to CH2Cl2:MeOH 5:1) to yield the title compound as a brown solid.

Aufarbeitung

  1. temperaturewarmed to 25° C.
  2. customquenched by NH4Cl (solid)
  3. additionEtOAc and water were then added to the mixture
  4. customThe reaction mixture was then partitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted three times with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield crude material
  11. customThe crude material was purified by silica gel (EtOAc to CH2Cl2:MeOH 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c2e53efc2f343d19b3a34b8ee9ba7b1
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318766B2

Notizen zur Reaktion

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