Sodium Carbonate → methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

HRID 1518253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518253
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:10](Br)[NH:11]2)=[CH:7][CH:6]=1)=[O:4].N1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30](OC)=[O:31])[CH:28]=2)C=C1.OCC1C=CC=CC=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.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.O1CCOCC1>[CH:15]1([C:9]2[C:8]3[C:12](=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[NH:11][C:10]=2[C:26]2[CH:25]=[CH:24][CH:29]=[CH:28][C:27]=2[CH2:30][OH:31])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 639844Methyl indole-6-carboxylateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Produkt 1

HCID 58677008methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-bromo-3-cyclohexyl indole-6-carboxylic acid methyl ester (1 eq., prepared as described in WO2004/087714 from commercially available methyl indole-6-carboxylate) was mixed with [2-(hydroxymethyl)phenyl]boronic acid (1.5 eq.) and bis(triphenylphosphine)palladium dichloride (0.2 eq.) was added. The mixture was degassed and dioxane and 2M aq. Na2CO3 solution (2 eq.) were added. The mixture was heated under N2-atmosphere to 110° C. for 1 h then diluted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was subjected to flash chromatography (PE:EtOAc, 4:1). After evaporation of the solvents the product was obtained as orange solid (95%). MS (ES+): 364.3 (M+H+).

Aufarbeitung

  1. additionwas added
  2. customThe mixture was degassed
  3. washwashed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated in vacuo
  6. customAfter evaporation of the solvents the product

Quellen und Nachweise

ORD-Eintrag
ord-a8bb84a1e4e04b6e86ddde4ca87af1dd
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232390B2

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