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 1267242노트

반응식

HRID 1267242 반응식
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

참가 물질

5

반응물 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

생성물 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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9d6cadb4d33475884952b42f1236134
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552049B2

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