(E)-5-(2-Methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine → 6-Methyl-5-(pyrimidin-5-yloxy)-1H-indole

HRID 2361250Notes

Reaction equation

HRID 2361250 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([N+]([O-])=O)[C:12](/[CH:18]=[CH:19]/[N:20]2CCCC2)=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1>CO.[Pd]>[CH3:1][C:2]1[CH:14]=[C:13]2[C:12]([CH:18]=[CH:19][NH:20]2)=[CH:11][C:3]=1[O:4][C:5]1[CH:10]=[N:9][CH:8]=[N:7][CH:6]=1

Participants

4

Reactant 1

HCID 86681515(E)-5-(2-Methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine

Product 1

HCID 679952196-Methyl-5-(pyrimidin-5-yloxy)-1H-indoleYield 46.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A red, heterogeneous solution of (E)-5-(2-methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine (0.963 g, 2.95 mmol) and 10% Pd/C (0.314 g, 0.295 mmol) in methanol (49.2 mL) was hydrogenated overnight. The reaction was flushed with nitrogen, filtered through a pad of CELITE®, and rinsed with MeOH. The filtrate was concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 40 g column eluting with 0-5% MeOH/CH2Cl2. Appropriate fractions were collected and concentrated in vacuo to the desired product (0.3082 g, 1.37 mmol, 46.4%) as a light yellow solid.

Workup

  1. customThe reaction was flushed with nitrogen
  2. filtrationfiltered through a pad of CELITE®
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a residue which
  6. customwas purified by flash chromatography
  7. washeluting with 0-5% MeOH/CH2Cl2
  8. customAppropriate fractions were collected

Sources & evidence

ORD record
ord-203c56fabdd14902b6330c07baa3051f
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…