3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 9887233, compound

HRID 584597Notes

Reaction equation

HRID 584597 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:5]([N:16]=1)=[C:6]1[C:11](=[CH:12][CH:13]=2)[O:10][CH2:9][C@H:8]([CH2:14]Cl)[O:7]1.[NH:17]1[CH2:22][CH:21]=[C:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:19][CH2:18]1>CS(C)=O.C(OCC)(=O)C>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([C:20]2[CH2:21][CH2:22][N:17]([CH2:14][CH:8]3[O:7][C:6]4[C:11](=[CH:12][CH:13]=[C:4]5[NH:3][C:2]([CH3:1])=[N:16][C:5]5=4)[O:10][CH2:9]3)[CH2:18][CH:19]=2)=[CH:24]1

Participants

5

Reactant 2

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 11447789HCID 11447789, compound

Product 1

HCID 9887233HCID 9887233, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 0.50 g (2.1 mmole) of [(8R)-2-methyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-yl]methyl chloride 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 100-110° 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 1% methanol in chloroform as eluant and the product fractions concentrated in vacuum to give the desired compound as the free base. Recrystallization from ethanol with the addition of 0.12 g of fumaric acid gave 0.11 g of the (S)-enantiomer of the title compound as a yellow solid fumarate, one-quarter hydrate, m.p. 219-222° 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 1% methanol in chloroform as eluant
  7. concentrationthe product fractions concentrated in vacuum

Sources & evidence

ORD record
ord-9a9097337b0541779e8c31637769ace0
Source dataset
uspto-grants-2005_08
Patent number
US06927226B2

Reaction notes

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