3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 10273241, compound

HRID 584601Notes

Reaction equation

HRID 584601 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][C:24]([CH2:26][CH3:27])=[N:23][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][C:24]([CH2:26][CH3:27])=[N:23][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 86586538HCID 86586538, compound

Product 1

HCID 10273241HCID 10273241, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.84 g (2.2 mmole) of [(8R)-2-ethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-yl]methyl 4-methylbenzenesulfonate and 1.5 g (7.60 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole in 10.0 mL of DMSO was heated at 80° 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 0.53 g of the desired compound as the free base. Recrystallization from ethanol with the addition of one equivalent of fumaric acid gave 0.46 g of the (S)-enantiomer of the title compound as a pale yellow solid fumarate, m.p. 231-232° 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-f3d8c35e2b38423fa934d2a2f2190ff1
Source dataset
uspto-grants-2005_08
Patent number
US06927226B2

Reaction notes

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