HCID 67093431, compound → HCID 58215558, compound

HRID 1661716Notes

Reaction equation

HRID 1661716 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]([CH3:20])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]=[N:9][CH:10]=1>[Pd].CO>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]([CH3:20])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]=[N:9][CH:10]=1

Participants

4

Reactant 1

HCID 67093431HCID 67093431, compound

Product 1

HCID 58215558HCID 58215558, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A flask is charged with 2-[5-(2-methoxy-vinyl)-pyridin-3-yl]-1-methyl-1H-indole (0.550 g, 2.08 mmol) and methanol (5 mL). Palladium on carbon (0.221 g, 0.208 mmol) is added and the reaction mixture is stirred at 50° C. under H2 for 16 h. It is then cooled to room temperature and filtered through celite. The celite layer is thoroughly washed with methanol. The filtrate is concentrated in vacuo, to give a residue which is purified by silica gel flash chromatography (heptane-ethyl acetate, 7:3) to afford 2-[5-(2-methoxy-ethyl)-pyridin-3-yl]-1-methyl-1H-indole as an oil. MS (ESI) m/z 267.36 (M+H)+.

Workup

  1. temperatureIt is then cooled to room temperature
  2. filtrationfiltered through celite
  3. washThe celite layer is thoroughly washed with methanol
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto give a residue which
  6. customis purified by silica gel flash chromatography (heptane-ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-df4a1bec07f143288dd4e1f61481b79b
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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