(3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)(morpholino)methanone → (3-(2-Amino-1-(2-fluorophenyl)ethyl)-1H-indol-6-yl)(morpholino)methanone

HRID 2361243Notes

Reaction equation

HRID 2361243 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]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:9][N+:10]([O-])=O>CO.[Ni]>[NH2:10][CH2:9][CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 67994854(3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 67994639(3-(2-Amino-1-(2-fluorophenyl)ethyl)-1H-indol-6-yl)(morpholino)methanoneYield 64.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a spatula full of Raney-Ni in a Parr tube was added a solution of (3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)(morpholino)methanone (0.3659 g, 0.921 mmol) in MeOH (30.7 mL). The reaction was shaken under hydrogenation at 53 psi for 3 hr. After flushing with nitrogen, the mixture was filtered through a pad of CELITE® and rinsed with MeOH. The filtrate was concentrated in vacuo to give the desired product (0.270 g, 0.596 mmol, 64.7% yield).

Workup

  1. customAfter flushing with nitrogen
  2. filtrationthe mixture was filtered through a pad of CELITE®
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b5398eb2fe7b44a48c81e9fdc40f8f07
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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