3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 22341387, compound

HRID 584599Notes

Reaction equation

HRID 584599 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]4[NH:25][CH:24]([CH3:26])[N:23]([CH3:27])[C:20]4=3)[O:15][CH2:14]2)(=O)=O)=CC=1.[NH:28]1[CH2:33][CH:32]=[C:31]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)[CH2:30][CH2:29]1>CS(C)=O.C(OCC)(=O)C>[NH:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34]([C:31]2[CH2:32][CH2:33][N:28]([CH2:12][CH:13]3[O:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]5[NH:25][CH:24]([CH3:26])[N:23]([CH3:27])[C:20]5=4)[O:15][CH2:14]3)[CH2:29][CH:30]=2)=[CH:35]1

Participants

5

Reactant 2

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 86590762HCID 86590762, compound

Product 1

HCID 22341387HCID 22341387, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 0.69 g (1.8 mmole) of [(8R)-1,2-dimethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-yl]methyl 4-methylbenzenesulfonate and 1.0 g (5.0 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole in 10.0 mL of DMSO was heated at 90-100° C. under nitrogen for 6 hours. The reaction was allowed to come to room temperature, diluted to 500 mL with ethyl acetate, washed with 400 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine, dried over sodium sulfate, filtered and evaporated in vacuum. The residue was column chromatographed on silica gel with 0-3% methanol in chloroform as eluant and the product fractions concentrated in vacuum to give 0.090 g of the desired compound as the free base. Recrystallization from ethanol with the addition of 0.025 g of fumaric acid gave the (S)-enantiomer of the title compound as a yellow solid, m.p. 186-188° C.

Workup

  1. customto come to room temperature
  2. washwashed with 400 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuum
  6. customchromatographed on silica gel with 0-3% methanol in chloroform as eluant
  7. concentrationthe product fractions concentrated in vacuum

Sources & evidence

ORD record
ord-6f8324cd0c4f4cf78600c6103458e4a1
Source dataset
uspto-grants-2005_08
Patent number
US06927226B2

Reaction notes

Loading…