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 1267242Notes

Reaction equation

HRID 1267242 reaction equation
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

Participants

5

Reactant 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

Product 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

Procedure

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 tetrahydrofuran/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.

Workup

  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

Sources & evidence

ORD record
ord-a9d6cadb4d33475884952b42f1236134
Source dataset
uspto-grants-2003_04
Patent number
US06552049B2

Reaction notes

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