Water → HCID 24700976, compound

HRID 2247489Notes

Reaction equation

HRID 2247489 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[C:4]([N+:13]([O-])=O)[CH:3]=1.[BH4-].[Na+].O.C(OCC)(=O)C>C(Cl)Cl.CO.O.O.O.O.O.O.[Ni]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[C:4]([NH2:13])[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 59333358HCID 59333358, compound

Product 1

HCID 24700976HCID 24700976, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 86602470HCID 86602470, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-2-nitro phenyl)-1H-imidazole (500 mg) in methylene chloride (10 mL) and methanol (10 mL) at 0° C. nickel hexahydrate (22.0 mg) and sodium borohydride (177 mg) were added one by one, and the reaction solution was agitated for 20 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH; elution solvent: hexane:ethyl acetate=1:1->ethyl acetate), and 431 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH; elution solvent: hexane:ethyl acetate=1:1->ethyl acetate)

Sources & evidence

ORD record
ord-e3d98fa2b4674c79b0ef63aee67eae98
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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