HCID 67203361, compound → 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine

HRID 85105Notes

Reaction equation

HRID 85105 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([NH:18]C(=O)OCC4C=CC=CC=4)[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1>CO.[Pd]>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([NH2:18])[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 67203361HCID 67203361, compound

Product 1

HCID 636906712-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of benzyl 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-ylcarbamate (12; 1.45 g, 3.5 mmol) in methanol (20 mL) was added 5% Pd/C (0.20 g). The reaction mixture was thoroughly purged with nitrogen and then stirred under 1 atm of hydrogen at room temperature for 18 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to give 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine 13 (0.90 g, 3.25 mmol, 93%) as a solid. MS (ESI) calcd for C14H10F3N3: 277.08; found: 278 [M+H].

Workup

  1. customThe reaction mixture was thoroughly purged with nitrogen
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d74ff526ab2c420b88d7e311f1b5f137
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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