Potassium Carbonate → 1-Benzyl-2-methyl-4-(3-(N-[isobutyl]-N-[cyano]amino)-4-nitrophenyl)-5-(2,4-difluorophenyl)-1H-imidazole

HRID 250745Notes

Reaction equation

HRID 250745 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[C:11](Br)[N:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([N:25]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:26]1[CH:31]=[C:30](B2OCC(C)(C)CO2)[CH:29]=[CH:28][C:27]=1[N+:40]([O-:42])=[O:41])#[N:24].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P([C-]1C=CC=C1)C(C)(C)C)(C)(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[C:11]([C:30]2[CH:29]=[CH:28][C:27]([N+:40]([O-:42])=[O:41])=[C:26]([N:25]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:23]#[N:24])[CH:31]=2)[N:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 179816721-benzyl-2-methyl bromo-5-(2,4-difluorophenyl)-1H-imidazoleHCID 86623267N-[cyano]N-[isobutyl]2-nitro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)aniline

Product 1

HCID 866232661-Benzyl-2-methyl-4-(3-(N-[isobutyl]-N-[cyano]amino)-4-nitrophenyl)-5-(2,4-difluorophenyl)-1H-imidazoleYield 42.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178454863HCID 178454863, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Heat 1-benzyl-2-methyl bromo-5-(2,4-difluorophenyl)-1H-imidazole (0.321 g, 0.885 mmol), N-[cyano]N-[isobutyl]2-nitro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)aniline (0.352 g, 1.06 mmol), palladium(II)acetate (0.0099 g, 0.044 mmol), di-tert-butylphosphinoferrocene (0.058 g, 0.177 mmol), and potassium carbonate (0.45 g, 3.26 mmol) in dioxane (10 mL) to 100° C. for 20 hours. Cool to room temperature and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures to provide 0.191 g (0.38 mmol) of the title compound.

Workup

  1. concentrationconcentrate under reduced pressure
  2. washSubject residue to silica gel chromatography, eluting with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-0f4b118e00c0413880119d2a0ebe518c
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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