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Carbon Dioxide → HCID 11492556, Verbindung

HRID 907124
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 907124
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=2.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1.[C:25](=[O:28])(O)[O-].[Na+].C(=O)=O>C(O)(=O)C.O>[N+:13]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:11]#[N:12])=[C:2]([N:1]3[CH:18]=[CH:22][CH:21]=[CH:20]3)[NH:3]2)=[CH:8][CH:7]=1)([O-:15])=[O:14].[CH2:18]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:28][CH3:25])[CH:5]=2)[C:10]([C:11]#[N:12])=[CH:2]1)[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 280Carbon DioxideHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 163613672-Amino-6-nitro-1H-indole-3-carbonitrile

Produkt 2

HCID 11492556HCID 11492556, VerbindungHCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-amino-6-nitro-1H-indole-3-carbonitrile (362 mg, 1.79 mmol) in acetic acid (5 mL) was treated with 2,5-dimethoxytetrahydrofuran (0.30 mL, 2.27 mmol), and the solution was heated to reflux for 14 h. After cooling to ambient temperature, the solution was poured into water (100 mL), and solid sodium bicarbonate was added until CO2 evolution ceased. The mixture was extracted with EtOAc (2×100 mL), and the extracts were washed with saturated brine, combined, dried over MgSO4, filtered and concentrated. The residual material was separated by silica gel chromatography (EtOAc/hexanes, 1/4) to afford 6-nitro-2-pyrrol-1-yl-1H-indole-3-carbonitrile, compound 5, as a yellow solid (232 mg, 51%).

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux for 14 h
  3. extractionThe mixture was extracted with EtOAc (2×100 mL)
  4. washthe extracts were washed with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual material was separated by silica gel chromatography (EtOAc/hexanes, 1/4)

Quellen und Nachweise

ORD-Eintrag
ord-88c94c076d1547f698634e383071db4a
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08013006B2

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