Sodium Carbonate → Methyl 2-{2-[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

HRID 1444627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444627
Br[C:2]1[N:3]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])O1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:50]([O:49][C:48]([NH:47][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[C:2]1[N:3]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)=[O:54])([CH3:51])([CH3:52])[CH3:53]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2773231tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 68501826methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

Produkt 1

HCID 68693096Methyl 2-{2-[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate in dioxane (0.15 M) was added Na2CO3 (4 eq, 2 M aqueous solution), tert-butyl [2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (1.5 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.2 eq). The mixture was heated at reflux for 45 mins. The reaction mixture was filtered and then the filtrate was diluted with EtOAc. The organic phase was washed with H2O, brine and dried over Na2SO4 before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (Biotage cartridge Si65i, 1:9 EtOAc/PE) to give the title compound as a white solid (60%); MS (ES+) m/z 535 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 45 mins
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate was diluted with EtOAc
  5. washThe organic phase was washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. filtrationbefore being filtered
  8. concentrationconcentrated in vacuo
  9. customThe crude was purified by flash chromatography (Biotage cartridge Si65i, 1:9 EtOAc/PE)

Quellen und Nachweise

ORD-Eintrag
ord-db38a8f74ac84d0caf3f717532961ecf
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662809B2

Notizen zur Reaktion

Wird geladen…