HCID 59304984, compound → HCID 59305028, compound

HRID 2240242Notes

Reaction equation

HRID 2240242 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[C:13]2[CH:20]=[CH:19][NH:18][C:14]=2[N:15]=[CH:16][CH:17]=1>O.C(O)C.[Fe](Cl)(Cl)Cl.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[NH:18][CH:19]=[CH:20][C:13]=12

Participants

6

Reactant 1

HCID 59304984HCID 59304984, compound

Product 1

HCID 59305028HCID 59305028, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 24380Iron chloride (FeCl3)CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Variant B: A solution of 10 mg (60 μmol) of iron(III) chloride in 2.40 ml of water and then 38 mg (170 μmol) of powdered iron are added to a solution of 16 mg (60 μmol) of N-(2-chloro-4-nitrophenyl)-1H-pyrrolo[2,3-b]pyridine-4-amine in 3.60 ml of ethanol. After 3 h of stirring at 80° C., the suspension is filtered through kieselguhr and the kieselguhr is washed with ethanol. The solvent is removed under reduced pressure and the residue is dissolved in a mixture of dichloromethane/methanol 10:1 and crudely purified by column filtration on silica gel. This gives 22 mg of a crude product which is directly reacted further without further purification.

Workup

  1. filtrationthe suspension is filtered through kieselguhr
  2. washthe kieselguhr is washed with ethanol
  3. customThe solvent is removed under reduced pressure
  4. dissolutionthe residue is dissolved in a mixture of dichloromethane/methanol 10:1
  5. filtrationcrudely purified by column filtration on silica gel
  6. customThis gives 22 mg of a crude product which is directly reacted further without further purification

Sources & evidence

ORD record
ord-b039e151b831433faa0d695a7955168d
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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