HCID 67093431, compound → HCID 58215558, compound

HRID 1630941Notes

Reaction equation

HRID 1630941 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-a83f1aedf267449ba83c873a87170b0c
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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