Methanol → HCID 17981678, compound

HRID 2252028Notes

Reaction equation

HRID 2252028 reaction equation
[CH2:1]([N:8]1[C:12]([Br:13])=[C:11]([Br:14])[N:10]=[C:9]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:12]([Br:13])=[C:11]([Br:14])[N:10]=[C:9]1[C:20]1[CH:19]=[CH:18][C:17]([F:16])=[CH:22][C:21]=1[F:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 27732411-Benzyl-2,4,5-tribromo-1H-imidazole

Product 1

HCID 17981678HCID 17981678, compoundYield 37.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reflux a mixture of 1-benzyl-2,4,5-tribromoimidazole (1.043 g, 2.42 mmol), 2,4-difluorophenyl boronic acid (0.682 g, 4.32 mmol), palladium acetate (0.027 g, 0.12 mmol), R(+)-2,2′-bis(di-p-tolyl-phosphino)1,1′-binaphthyl (0.098 g, 0.14 mmol), 2 M sodium carbonate (3.6 mL, 4.83 mmol), methanol (3.6 mL) and toluene (36 mL) for 18 hours. Cool to ambient temperature and dilute with ethyl acetate. Wash with saturated sodium carbonate, saturated sodium chloride, dry with magnesium sulfate and purify the residue on silica gel eluting with hexane/ethyl acetate mixtures to provide 1-benzyl-4,5-dibromo-2-(2,4-difluoro-phenyl)-1H-imidazole (0.39 g). MS(ES+): m/z=461.1 (M+H)+

Workup

  1. temperatureReflux
  2. washWash with saturated sodium carbonate, saturated sodium chloride
  3. dry with materialdry with magnesium sulfate
  4. custompurify the residue on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-10b6d84554584ab5bd461c0308ee02ef
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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