1,2-Dimethoxyethane → 1-Isopropylsulfonyl-2-amino-6-(1-(benzyl)-5-(3,5-difluorophenyl)-2-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazole

HRID 2252030Notes

Reaction equation

HRID 2252030 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)=[C:11](Br)[N:10]=[C:9]1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([S:33]([N:36]1[C:40]2[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[NH2:48])(=[O:35])=[O:34])([CH3:32])[CH3:31].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)(=O)C>[CH:30]([S:33]([N:36]1[C:40]2[CH:41]=[C:42]([C:11]3[N:10]=[C:9]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=4[F:29])[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12]=3[C:13]3[CH:14]=[C:15]([F:20])[CH:16]=[C:17]([F:19])[CH:18]=3)[CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[NH2:48])(=[O:34])=[O:35])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 179816431-Benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazoleHCID 17981723HCID 17981723, compound

Product 1

HCID 179817671-Isopropylsulfonyl-2-amino-6-(1-(benzyl)-5-(3,5-difluorophenyl)-2-(2,4-difluorophenyl)-imidazol-4-yl)-benzimidazoleYield 104.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Reflux a mixture of 1-benzyl-4-bromo-5-(3,5-difluoro-phenyl)-2-(2,4-difluoro-phenyl)-imidazole (0.061 g, 0.13 mmol), 1-isopropylsulfonyl-2-amino-benzimidazole-6-boronic acid (0.113 g, 0.40 mmol) (described in preparation 56), trans-dichlorobis(triphenylphosphine) palladium (II) (0.009 g, 0.013 mmol), 2 M sodium carbonate (0.20 mL) and 1,2-dimethoxyethane (5 mL) for 18 hours. Cool to ambient temperature, dilute with ethyl acetate and wash with saturated sodium bicarbonate, saturated sodium chloride, dry with magnesium sulfate, filter and remove solvents under reduced pressure. Purify on silica gel with dichloromethane/methanol mixtures to provide the title compound (0.084 g). MS(ES+): m/z=620.1 (M+H)+

Workup

  1. temperatureReflux
  2. washwash with saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdry with magnesium sulfate
  4. filtrationfilter
  5. customremove solvents under reduced pressure
  6. customPurify on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-d9a1b0db37434476ad9966d0cc4152a0
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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