Sodium Bicarbonate → methyl 3-cyclohexyl-2-{2-[2-(tetrahydropyran-2-yloxy)ethylsulfanyl]phenyl}-1H-indole-6-carboxylate

HRID 1012350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012350
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.C(=O)([O-])O.[Na+].[CH:23]1([C:29]2[C:37]3[C:32](=[CH:33][C:34]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:36]=3)[NH:31][C:30]=2B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:23]1([C:29]2[C:37]3[C:32](=[CH:33][C:34]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:36]=3)[NH:31][C:30]=2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 23152432methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylateHCID 231526382-[2-(2-Bromophenylsulfanyl)ethoxy]tetrahydropyran

Produkt 1

HCID 11995000methyl 3-cyclohexyl-2-{2-[2-(tetrahydropyran-2-yloxy)ethylsulfanyl]phenyl}-1H-indole-6-carboxylateAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-[2-(2-bromophenylsulfanyl)ethoxy]tetrahydropyran (1.00 g, 3.2 mmol), sodium hydrogen carbonate (1.10 g, 13.2 mmol) and tetrakis(triphenylphosphine)palladium (363 mg, 0.310 mmol) in 1,2-dimethoxyethane (10 ml) and water (5 ml) was added methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate (1.45 g, 3.78 mmol) with heating under reflux and the mixture was heated under reflux for 2.5 hr. The reaction mixture was allowed to cool to room temperature, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1-3:1) to give methyl 3-cyclohexyl-2-{2-[2-(tetrahydropyran-2-yloxy)ethylsulfanyl]phenyl}-1H-indole-6-carboxylate (1.38 g, yield 74.5%).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2.5 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was successively washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1-3:1)

Quellen und Nachweise

ORD-Eintrag
ord-75d4225e3d924076bf126982453527a0
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977331B1

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