Water → Dicyclopropyl[1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanol

HRID 1628943Notes

Reaction equation

HRID 1628943 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([C:22]([O:24]C)=O)[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11]1.[CH:26]1([Mg]Br)[CH2:28][CH2:27]1.O.O1[CH2:36][CH2:35][CH2:34]C1>>[CH:26]1([C:22]([CH:34]2[CH2:35][CH2:36]2)([C:18]2[C:17]3[N:13]4[CH2:12][CH2:11][N:10]([C:3]5[C:4]([CH3:9])=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=5[Cl:1])[C:14]4=[N:15][C:16]=3[CH:21]=[CH:20][CH:19]=2)[OH:24])[CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 57785884Methyl 1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylateHCID 178418630HCID 178418630, compound

Product 1

HCID 57786331Dicyclopropyl[1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl]methanolYield 39%

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate (90 mg, 0.239 mmol) in tetrahydrofuran (2.4 mL) was added a solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.0 M, 1.4 mL, 1.4 mmol) at room temperature. The mixture was stirred at 60° C. for 1.5 hr. Water was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 25-60% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/diisopropyl ether to give the title compound (40.2 mg, 0.094 mmol, 39%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 25-60% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-36efddfdd28945009e368c47176b2453
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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