Water → [8-Chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl](dicyclopropyl)methanol

HRID 1628940Notes

Reaction equation

HRID 1628940 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]([O:25]C)=O)=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=3[Cl:22])[CH2:12][CH2:13][N:7]21.[CH:27]1([Mg]Br)[CH2:29][CH2:28]1.O.O1[CH2:37][CH2:36][CH2:35]C1>>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=4[Cl:22])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([C:23]([CH:35]2[CH2:36][CH2:37]2)([CH:27]2[CH2:29][CH2:28]2)[OH:25])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 57785906Methyl 8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylateHCID 178418630HCID 178418630, compound

Product 1

HCID 57785972[8-Chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-5-yl](dicyclopropyl)methanolYield 30%

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate (90 mg, 0.219 mmol) in tetrahydrofuran (2.2 mL) was added a solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.0 M, 1.3 mL, 1.3 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 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 to give the title compound (29.9 mg, 0.065 mmol, 30%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over 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

Sources & evidence

ORD record
ord-ee56e953787245d8b0fadd0633043a92
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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