Pyridine → [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-carbamic acid 2-(2-methoxy-ethoxy)-ethyl ester

HRID 502264

Reaktionsgleichung

Reaktionsgleichung von HRID 502264
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:22]3[CH2:25][CH2:24][CH2:23]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:27]([O:29][C:30]1[CH:35]=CC([N+]([O-])=O)=CC=1)=[O:28].N1C=CC=CC=1.[CH3:45][O:46][CH2:47][CH2:48][O:49]CCO>C(Cl)Cl.ClCCCl>[CH3:45][O:46][CH2:47][CH2:48][O:49][CH2:35][CH2:30][O:29][C:27](=[O:28])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:22]3[CH2:23][CH2:24][CH2:25]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 8134Diethylene Glycol Monomethyl EtherHCID 821294-Nitrophenyl chloroformateHCID 250520112-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-indole-3-carbonitrile

Produkt 1

HCID 59425495[4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-carbamic acid 2-(2-methoxy-ethoxy)-ethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (40 mg, 0.12 mmol), prepared as in example 1CM, step B, is combined with 4-nitrophenyl chloroformate (60 mg, 0.30 mmol), DCE (0.4 mL), and pyridine (25 μL, 0.31 mmol). This suspension is stirred at room temperature for 1 h. 2-(2-methoxyethoxy)ethanol (150 μL, 1.25 mmol) is added. This mixture is heated at 80° C. overnight. The reaction mixture is then diluted in CH2Cl2 and is washed with dilute aqueous NaOH to remove the yellow nitrophenol by-product. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2) yields [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-carbamic acid 2-(2-methoxy-ethoxy)-ethyl ester (51 mg, 89%) as a white solid.

Aufarbeitung

  1. temperatureThis mixture is heated at 80° C. overnight
  2. washis washed with dilute aqueous NaOH
  3. customto remove the yellow nitrophenol by-product
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-a388e017587f412f92fdb2763ae481e5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

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