Carbon tetrabromide → [4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-bromomethyl-piperidin-1-yl]-methanone

HRID 31521Notes

Reaction equation

HRID 31521 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:28]O)[CH2:24][CH2:23]3)=[O:21])[C:10]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=3[O:40][CH2:41][CH3:42])=[N:9]2)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:28][Br:44])[CH2:24][CH2:23]3)=[O:21])[C:10]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=3[O:40][CH2:41][CH3:42])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69273741[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-hydroxymethyl-piperidin-1-yl]-methanone

Product 1

HCID 86595530[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-bromomethyl-piperidin-1-yl]-methanoneYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-hydroxy methyl-piperidin-1-yl]-methanone (60 mg, 0.096 mmol) in methylene chloride (2 mL) was added carbon tetrabromide (70 mg, 0.210 mmol) followed by triphenyl phosphine (55 mg, 0.21 mmol). The reaction mixture was stirred at ambient temperature for 2.5 h. The reaction was diluted with water and extracted with methylene chloride. The organic extracts were washed with water, brine, and dried over anhydrous sodium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel using 1-5% methanol in methylene chloride gave [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-bromomethyl-piperidin-1-yl]-methanone (50 mg, 76%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvents and chromatography of the residue over silica gel using 1-5% methanol in methylene chloride

Sources & evidence

ORD record
ord-e86c723c78e44ff882278e94b25c4d25
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Reaction notes

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