Methylamine → HCID 68701570, Verbindung

HRID 42661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42661
[CH3:1][NH2:2].O=[C:4]([C:11]1[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:34][C:35]1[CH:36]=[C:37]([C:52](=O)[CH2:53]Br)[CH:38]=[C:39]([N+:49]([O-:51])=[O:50])[C:40]=1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)C.C(O)(=O)C.CN(C)C=O>[CH2:27]([O:34][C:35]1[CH:36]=[C:37]([C:52]2[N:2]([CH3:1])[C:4]([C:11]3[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][CH:14]=[CH:15][CH:16]=3)=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:53]=2)[CH:38]=[C:39]([N+:49]([O-:51])=[O:50])[C:40]=1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

8

Edukt 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 68702337HCID 68702337, VerbindungHCID 714457901-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2-bromoethan-1-one

Produkt 1

HCID 68701570HCID 68701570, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of methylamine (0.63 mL, 33% EtOH solution, 5 mmol) in a mixture of ethanol (25 mL) and acetic acid (0.5 mL) at room temperature was added ethyl 3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoate (1.305 g, 5 mmol). The reaction mixture was heated at reflux for two hours whereupon the solvent was removed by evaporation under vacuum. To a solution of the crude product in dimethylformamide (25 mL) was added potassium carbonate (2.07 g, 15 mmol) in one portion followed by 1-(3,4-bis-benzyloxy-5-nitro-phenyl)-2-bromo-ethanone (2.51 g, 5.50 mmol) and the mixture was then stirred at 100° C. Once no starting material was detectable, the reaction mixture was allowed to cool to room temperature and poured onto ice-cold 1 N aqueous hydrochloric acid (100 mL). The resulting precipitate was filtered off, washed with water and dried. The residue was chromatographed over silica gel. Homogeneous fractions were pooled and evaporated to give ethyl 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate, 2.492 g (79%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for two hours whereupon the solvent
  3. customwas removed by evaporation under vacuum
  4. temperatureto cool to room temperature
  5. additionpoured onto ice-cold 1 N aqueous hydrochloric acid (100 mL)
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customThe residue was chromatographed over silica gel
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a3df68da885f4037b288775b0fd2c54d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536203B2

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