N-(2-amino-phenyl)-5-bromo-2-fluoro-benzamide → 2-(5-Bromo-2-fluoro-phenyl)-1H-benzoimidazole

HRID 2047388Notes

Reaction equation

HRID 2047388 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[F:17]>C(O)(=O)C>[Br:16][C:14]1[CH:13]=[CH:12][C:11]([F:17])=[C:10]([C:9]2[NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:15]=1

Participants

3

Reactant 1

HCID 24693313N-(2-amino-phenyl)-5-bromo-2-fluoro-benzamide

Product 1

HCID 432364512-(5-Bromo-2-fluoro-phenyl)-1H-benzoimidazoleYield 89.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(2-amino-phenyl)-5-bromo-2-fluoro-benzamide (5.64 g, 18.3 mmol) in acetic acid (20 mL) was heated at 60° C. After 30 min, the suspension became a solution and it was left overnight. The solvent was removed under reduced pressure and residue was triturated with DCM (10 mL) and filtered off. The precipitate was washed with DCM (3×10 mL) and dried to afford 4.76 g of the title compound (89%).

Workup

  1. waitwas left overnight
  2. customThe solvent was removed under reduced pressure and residue
  3. customwas triturated with DCM (10 mL)
  4. filtrationfiltered off
  5. washThe precipitate was washed with DCM (3×10 mL)
  6. customdried

Sources & evidence

ORD record
ord-a0020226a2894bd2a1ecc68c4a8d1139
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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