4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

HRID 576155Notes

Reaction equation

HRID 576155 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=2)[CH:6]=1>CO.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=2)[NH2:17])[CH:6]=1

Participants

4

Reactant 1

HCID 177482064-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole

Product 1

HCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)anilineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole (800 mg, 2.95 mmol) in MeOH (15 mL) was added to a solution of palladium (5.02 μL, 0.078 mmol) in MeOH (15 mL). The mixture was at 25° C. for 5 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative HPLC (MeCN/H2O as eluants, basic condition) to yield a white solid of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (321.83 mg, 1.334 mmol, 86.0% yield). TLC (PE/EA=1:1, Rf=0.3): 1H NMR (400 MHz, CD3OD) δ 7.98 (s, 1H), 7.24 (s, 1H), 7.02-6.76 (m, 3H), 2.31-2.17 (m, 3H); ES-LCMS m/z 242.1 (M+H).

Workup

  1. concentrationThen the solution was concentrated
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by preparative HPLC (MeCN/H2O as eluants, basic condition)

Sources & evidence

ORD record
ord-d273f203b99747e5a8221be2418b0b1d
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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