3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 10161338, compound

HRID 1743111Notes

Reaction equation

HRID 1743111 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:30][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH2:26][CH3:27])[C:20]([CH2:28][CH3:29])=[N:19]4)(=O)=O)=CC=1.[NH:31]1[CH2:36][CH:35]=[C:34]([C:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][CH:38]=2)[CH2:33][CH2:32]1>CS(C)=O.C(OCC)(=O)C>[CH2:26]([C:21]1[C:20]([CH2:28][CH3:29])=[N:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14][CH:13]([CH2:12][N:31]4[CH2:32][CH:33]=[C:34]([C:37]5[C:45]6[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=6)[NH:39][CH:38]=5)[CH2:35][CH2:36]4)[O:30][C:17]3=2)[N:22]=1)[CH3:27]

Participants

5

Reactant 2

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 12082523HCID 12082523, compound

Product 1

HCID 10161338HCID 10161338, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2R)-8,9-diethyl-2,3-dihydro[1,4]dioxino[2,3-f]-quinoxalin-2-ylmethyl 4-methylbenzenesulfonate (0.300 g, 0.700 mmole) in methyl sulfoxide (20 mL) was added 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.555 g, 2.800 mmole) and the reaction mixture was heated to 80° C. for 12 hours. The reaction mixture was allowed to cool to room temperature and was diluted with ethyl acetate (250 mL), washed with water (2×100 mL), aqueous sodium chloride (100 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, methanol:ethyl acetate 1:9) followed by recrystallization from ethanol provided 0.184 g (58%) of the (S)-enantiomer of the title compound as a yellow crystalline solid. Rf=0.41 (silica, methanol:ethyl acetate 1:9); mp>120° C. dec.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with water (2×100 mL), aqueous sodium chloride (100 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customto give a crude solid
  6. customPurification by flash column chromatography (silica, methanol:ethyl acetate 1:9)
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-ab2abf8c9c2d4f358c86609839fcf21c
Source dataset
uspto-grants-2006_03
Patent number
US07008944B2

Reaction notes

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