Potassium Carbonate → 3-(1-{[8-Methyl-2,3-dihydrofuro[2,3-f][1,4]benzodioxin-2-yl]methyl}-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

HRID 49245

Reaktionsgleichung

Reaktionsgleichung von HRID 49245
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:18][O:17][C:16]3[CH:19]=[CH:20][C:21]4OC(C)=C[C:22]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.[NH:27]1[CH2:32][CH:31]=[C:30]([C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][CH:34]=2)[CH2:29][CH2:28]1.[C:42](=O)([O-])[O-].[K+].[K+].[O:48]1[CH2:52][CH2:51]CC1.CN(C)C=O>>[CH3:42][C:52]1[O:48][C:22]2[C:15]3[O:14][CH:13]([CH2:12][N:27]4[CH2:28][CH:29]=[C:30]([C:33]5[C:41]6[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=6)[NH:35][CH:34]=5)[CH2:31][CH2:32]4)[CH2:18][O:17][C:16]=3[CH:19]=[CH:20][C:21]=2[CH:51]=1

Komponenten

5

Edukt 4

HCID 11430Potassium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 86586532[(2R)-8-methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Produkt 1

HCID 185460253-(1-{[8-Methyl-2,3-dihydrofuro[2,3-f][1,4]benzodioxin-2-yl]methyl}-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Versuchsvorschrift

To a solution of 0.28 g (0.75 mmole) of [(2R)-8-methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methyl 4-methylbenzenesulfonate and 0.45 g (2.3 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole in 10 mL of 1:1 tetrahydro-furan/dimethylformamide was added 1.5 g (1.1 mmole) of potassium carbonate and the mixture was refluxed under nitrogen for 15 hours. Upon cooling to room temperature, the reaction mixture was filtered and the filtrate concentrated in vacuum. The residue was column chromatographed on silica gel with 50% hexane/ethyl acetate to give 0.13 g of the (S)-enantiomer of the title compound as a yellow solid, m.p. 198-200° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed under nitrogen for 15 hours
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuum
  4. customchromatographed on silica gel with 50% hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fb4b20de10694dfda0c97123d69d6b41
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706736B2

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