5-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole → 5-fluoro-3-(2-pyridin-3-yl-ethyl)-1H-indole

HRID 2382046Notes

Reaction equation

HRID 2382046 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[CH:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 685566735-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole

Product 1

HCID 685543805-fluoro-3-(2-pyridin-3-yl-ethyl)-1H-indoleYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-fluoro-3-(2-pyridin-3-yl-vinyl)-1H-indole (3 mmol) in MeOH (10 mL) is treated with Pd/C (200 mg) and shaken in a Parr apparatus under 40 atm of H2 for 18 h. The mixture is filtered through Celite and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0%-10% MeOH in DCM to afford 5-fluoro-3-(2-pyridin-3-yl-ethyl)-1H-indole (360 mg, 50%, 2 steps).

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 0%-10% MeOH in DCM

Sources & evidence

ORD record
ord-dff4e11dd51545a3a3b5a51217f55027
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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