Sodium Carbonate → HCID 86627906, Verbindung

HRID 1669475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669475
Br[C:2]1[NH:3][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.[CH:21]([C:23]1[C:24]([O:32][CH3:33])=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C([O-])([O-])=O.[Na+].[Na+]>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>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([CH:21]=[O:22])[C:24]=2[O:32][CH3:33])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateHCID 16218167(3-Formyl-2-methoxyphenyl)boronic acid

Produkt 1

HCID 86627906HCID 86627906, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (3-formyl-2-methoxyphenyl) boronic acid (1.5 eq) and Pd(PPh3)2Cl2 (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with Ar. 2M Na2CO3 solution (1 eq) was added and the mixture was heated to 110° C. for 2 h. All volatiles were evaporated in vacuo and the residual material was dissolved in EtOAc, filtered over Celite and evaporated in vacuo. The residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1). After evaporation of the fractions containing product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate was obtained as off-white solid (77%). (ES+) m/z 392 (M+H)+.

Aufarbeitung

  1. customThe solution was degassed
  2. customflushed with Ar
  3. customAll volatiles were evaporated in vacuo
  4. dissolutionthe residual material was dissolved in EtOAc
  5. filtrationfiltered over Celite
  6. customevaporated in vacuo
  7. filtrationThe residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1)
  8. customAfter evaporation of the fractions
  9. additioncontaining product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-1H-indole-6-carboxylate

Quellen und Nachweise

ORD-Eintrag
ord-bfee15f67e3a4700bec296c174cf6635
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989438B2

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