1,1'-Carbonyldiimidazole → HCID 178505197, compound

HRID 1890320Notes

Reaction equation

HRID 1890320 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][C:23]([F:26])([F:25])[F:24])[N:7]=1)(=[O:4])=[O:3].C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1>CO.[Pd]>[CH3:1][S:2]([O:5][C:6]1[N:7]=[C:8]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][C:23]([F:26])([F:25])[F:24])[C:32]([OH:33])=[N:12][C:9]2=[CH:10][CH:11]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86655256HCID 86655256, compound

Product 1

HCID 178505197HCID 178505197, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Nitro-6-(2-(trifluoromethoxy)phenylamino)pyridin-2-yl methanesulfonate (1.8 g, 4.58 mmol) was dissolved in MeOH (45 mL) and catalytic amount of 10% Pd/C was added. The reaction flask was purged with nitrogen and placed under an atmosphere of hydrogen for 2 h. The reaction mixture was filtered through Celite® and the solvent was removed under reduced pressure. The residue was immediately dissolved in THF (35 mL) and CDI (1.8 g, 11.0 mmol) added. The mixture was stirred overnight and concentrated under reduced pressure. The residue was added EtOAc, washed with water and 1 M HCl, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.1 g). LCMS m/z=390.3 [M+H]+.

Workup

  1. customThe reaction flask was purged with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite®
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was immediately dissolved in THF (35 mL)
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was added EtOAc
  7. washwashed with water and 1 M HCl
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-74052a6f5b1d4df282bba26d0d858714
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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