3-(1-(2-Fluorophenyl)-2-nitroethyl)-6-methyl-5-(pyrimidin-5-yloxy)-1H-indole → 2-(2-Fluorophenyl)-2-(6-methyl-5-(pyrimidin-5-yloxy)-1H-indol-3-yl)ethanamine

HRID 2361252Notes

Reaction equation

HRID 2361252 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([CH3:29])=[C:19]([O:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)[CH:20]=2)[NH:15][CH:14]=1)[CH2:9][N+:10]([O-])=O>CO.[Ni]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([CH3:29])=[C:19]([O:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)[CH:20]=2)[NH:15][CH:14]=1)[CH2:9][NH2:10]

Participants

4

Reactant 1

HCID 679947523-(1-(2-Fluorophenyl)-2-nitroethyl)-6-methyl-5-(pyrimidin-5-yloxy)-1H-indole

Product 1

HCID 679946462-(2-Fluorophenyl)-2-(6-methyl-5-(pyrimidin-5-yloxy)-1H-indol-3-yl)ethanamineYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a spatula of Raney-Ni in a hydrogenation flask was added 3-(1-(2-fluorophenyl)-2-nitroethyl)-6-methyl-5-(pyrimidin-5-yloxy)-1H-indole (0.284 g, 0.724 mmol) in methanol (12.06 mL). The reaction was hydrogenated at 53 psi. After 3 hr, the vessel was evacuated and flushed with nitrogen. The solution was filtered through a pad of CELITE® and rinsed with MeOH. The filtrate was concentrated in vacuo, dissolved in CH2Cl2, dried over Na2SO4, filtered and concentrated in vacuo to give the desired product (0.2405 g, 0.664 mmol, 92% yield).

Workup

  1. customthe vessel was evacuated
  2. customflushed with nitrogen
  3. filtrationThe solution was filtered through a pad of CELITE®
  4. washrinsed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutiondissolved in CH2Cl2
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1977d72ca4a84360b5d66b665e72528a
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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