HCID 58215610, compound → HCID 58215645, compound

HRID 1630865Notes

Reaction equation

HRID 1630865 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:17]=[CH2:18])[CH:16]=1>CO.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1

Participants

4

Reactant 1

HCID 58215610HCID 58215610, compound

Product 1

HCID 58215645HCID 58215645, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1-methyl-2-(5-vinyl-pyridin-3-yl)-1H-indole (Example 105, 0.473 g, 2.02 mmol) in methanol (10 mL) is added palladium on carbon (0.215 g, 0.202 mmol). The reaction mixture is stirred at 55° C. under H2 for 16 h. It is then cooled to room temperature and filtered through celite. The celite layer is washed with methanol thoroughly and the combined filtrate is concentrated in vacuo. The residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 3:1) to afford 1-methyl-2-(5-ethyl-pyridin-3-yl)-1H-indole as a yellow oil. MS (ESI) m/z 237.24 (M+H)+.

Workup

  1. temperatureIt is then cooled to room temperature
  2. filtrationfiltered through celite
  3. washThe celite layer is washed with methanol thoroughly
  4. concentrationthe combined filtrate is concentrated in vacuo
  5. customThe residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-18783436cbbf476381c7c83ccb46697b
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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