HCID 178526540, compound → HCID 178507436, compound

HRID 2218417Notes

Reaction equation

HRID 2218417 reaction equation
[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1>CO.[Ni]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:8][C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[C:3]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:4]3[N:10]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 178526540HCID 178526540, compound

Product 1

HCID 178507436HCID 178507436, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6-Chloro-2-(4-nitrophenyl)-N-phenyl-3H-imidazo[4,5-b]pyridin-7-amine (0.35 g, 1.0 mmol) was dissolved in 50 ml methanol. A catalytic amount of Raney-Nickel was added. The solution was shaken for 45 min under hydrogen pressure (3 atm). The catalyst was filtered off and the solvent removed in vacuo. The crude product was purified by column chromatography on silica, eluting with EtOAc/MeOH 9:1, giving the title product (0.29 g, 85%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed in vacuo
  3. customThe crude product was purified by column chromatography on silica
  4. washeluting with EtOAc/MeOH 9:1

Sources & evidence

ORD record
ord-aae78e34bdf9472e81a64b3652b88977
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

Loading…