3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 22663114, compound

HRID 392128Notes

Reaction equation

HRID 392128 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:25][C:24]3[C:20]4=[CH:21][O:22][N:23]=[C:19]4[CH:18]=[CH:17][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[NH:26]1[CH2:31][CH:30]=[C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:28][CH2:27]1>CS(C)=O>[NH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32]([C:29]2[CH2:30][CH2:31][N:26]([CH2:12][CH:13]3[O:25][C:24]4[C:20]5=[CH:21][O:22][N:23]=[C:19]5[CH:18]=[CH:17][C:16]=4[O:15][CH2:14]3)[CH2:27][CH:28]=2)=[CH:33]1

Participants

4

Reactant 2

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 86586940HCID 86586940, compound

Product 1

HCID 22663114HCID 22663114, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
77.5 °C

Procedure

(2R)-2,3-Dihydro[1,4]dioxino[2,3-e][2,1]benzisoxazol-2-ylmethyl 4-methyl-benzenesulfonate (0.60 g, 1.66 mmole) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.98 g, 4.90 mmole) were combined in 30 mL of DMSO under nitrogen. This solution was heated to 75-80° C. under nitrogen for 6 hours. After completion, the reaction was cooled to room temperature and partitioned between 400 mL each of ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was removed and washed with brine, dried over magnesium sulfate and concentrated in vacuum. The crude residue was column chromatographed on silica gel using methylene chloride to remove impurities and 1% methanol/methylene chloride to elute the product. Upon evaporation of the product fractions, 0.47 g (73%) of the (S)-enantiomer of the title compound was obtained as a white solid, m.p. 110° C.

Workup

  1. temperatureAfter completion, the reaction was cooled to room temperature
  2. custompartitioned between 400 mL each of ethyl acetate and saturated aqueous sodium bicarbonate
  3. customThe organic phase was removed
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel
  8. customto remove impurities and 1% methanol/methylene chloride
  9. washto elute the product
  10. customUpon evaporation of the product fractions, 0.47 g (73%) of the (S)-enantiomer of the title compound
  11. customwas obtained as a white solid, m.p. 110° C.

Sources & evidence

ORD record
ord-8c68ae08e7434b5faeaccafcedb7f729
Source dataset
uspto-grants-2004_10
Patent number
US06800642B2

Reaction notes

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