1,1'-Carbonyldiimidazole → HCID 67312878, compound

HRID 1890331Notes

Reaction equation

HRID 1890331 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:12]([N+:23]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1>CO.[Ni]>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:31](=[O:32])[NH:23][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67311982HCID 67311982, compound

Product 1

HCID 67312878HCID 67312878, compoundYield 121.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(benzyloxy)-N-(2-chlorophenyl)-3-nitropyridin-2-amine (750 mg, 2.11 mmol) in MeOH (20 mL) was added Raney nickel (300 mg). The reaction mixture was stirred overnight under H2 (1 atm), filtered through Celite® and concentrated. The residue was dissolved in DCM (40 mL) and CDI (410 mg, 2.53 mmol) was added. The mixture was stirred at room temperature for 4 h, washed with saturated NaHCO3 and water, dried over MgSO4 and concentrated to give the title compound (905 mg). LCMS m/z=352.3, [M+H]+.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM (40 mL)
  4. stirringThe mixture was stirred at room temperature for 4 h
  5. washwashed with saturated NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc48fc43ea5e4539935814094e5a289f
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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