Potassium Carbonate → {4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-carbamic acid 4-methoxy-phenyl ester

HRID 502258

Reaktionsgleichung

Reaktionsgleichung von HRID 502258
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:24]3[CH2:27][CH2:26][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][CH2:21][O:22][CH3:23])[CH:11]=3)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:36]>CCOC(C)=O>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([O:37][C:35](=[O:36])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]([CH:24]4[CH2:27][CH2:26][CH2:25]4)[C:10]4[C:15]([C:16]=3[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:11]=4)=[CH:6][CH:7]=2)=[CH:39][CH:40]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 82128Carbonochloridic acid, 4-methoxyphenyl esterHCID 594253792-(4-aminophenyl)-1-cyclobutyl-6-(2-methoxyethoxy)-1H-indole-3-carbonitrile

Produkt 1

HCID 59426020{4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-carbamic acid 4-methoxy-phenyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution 2-(4-aminophenyl)-1-cyclobutyl-6-(2-methoxyethoxy)-1H-indole-3-carbonitrile (530 mg, 1.58 mmol) in EtOAc (10 mL) is added 2M aqueous K2CO3 (556 uL, 5.9 mmol) and 4-methoxyphenyl chloroformate over a period of 5 min. The reaction mixture is stirred further for 3 h at room temperature. The reaction mixture is diluted with EtOAc (20 mL) and then washed with water (5 mL). The solvents are removed under reduced pressure and the residue is dissolved in EtOAc and then triturated with hexane. The precipitate is collected by filtration and washed with 50% EtOAc/hexane and dried in vacuo to afford {4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-carbamic acid 4-methoxy-phenyl ester (761 mg, 98%).

Aufarbeitung

  1. washwashed with water (5 mL)
  2. customThe solvents are removed under reduced pressure
  3. dissolutionthe residue is dissolved in EtOAc
  4. customtriturated with hexane
  5. filtrationThe precipitate is collected by filtration
  6. washwashed with 50% EtOAc/hexane
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-75ef6ea2c74c434c889759604b4c4893
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

Verknüpfte Notizen

Wird geladen…