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Iodoethane → Methyl 6-(6-chloro-5-ethoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

HRID 1191685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1191685
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[OH:28].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH3:36]>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:28][CH2:35][CH3:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69670789Methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

Produkt 1

HCID 69674219Methyl 6-(6-chloro-5-ethoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate (100 mg) in N,N-dimethylformamide (1 mL) were added, potassium carbonate (70.4 mg) and ethyl iodide (0.031 mL) and the mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (83.9 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d6c9deb27bff47188c7916025bbf806c
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680120B2

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