HCID 178526544, compound → HCID 178507444, compound

HRID 379529Notes

Reaction equation

HRID 379529 reaction equation
[N+:1]([C:4]1[C:12]2[NH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:12]2[NH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 178526544HCID 178526544, compound

Product 1

HCID 178507444HCID 178507444, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-nitro-2-trifluoromethylbenzimidazole (700 mg, 3.0 mmol) in methanol(50 ml)and was added 10% Pd/C (200 mg). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (10%MeOH/CH2Cl2) gave the desired product (560 mg, 93%). 1H NMR (CD3SO2CD3): δ10.49 (s, 1H), 7.09 (t, 1H), 6.72 (d, 1H), 6.30 (d, 1H), 5.52 (bs, 2H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-13374b87c0b040b5866d1a22ced86171
Source dataset
uspto-grants-2001_10
Patent number
US06300325B1

Reaction notes

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