Water → HCID 57786269, compound

HRID 1399294Notes

Reaction equation

HRID 1399294 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:22](OC)=[O:23])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[CH2:12][CH2:13][N:7]21.[CH:26]1([Mg]Br)[CH2:28][CH2:27]1.O.O1[CH2:36][CH2:35][CH2:34]C1>>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=4[Cl:21])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([C:22]([CH:34]2[CH2:35][CH2:36]2)([CH:26]2[CH2:28][CH2:27]2)[OH:23])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 57786058HCID 57786058, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 57786269HCID 57786269, compoundYield 57%

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 8-chloro-1-(2,4-dichlorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate (100 mg, 0.25 mmol) in tetrahydrofuran (2.5 mL) was added a solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.0 M, 1.5 mL, 1.5 mmol) at 0° C. 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 passed through the silica gel pad eluting with ethyl acetate and recrystallized from ethyl acetate to give the title compound (64.4 mg, 0.144 mmol, 57%) 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. washeluting with ethyl acetate
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-56d2c61b34a94e17892f53aa8855ce22
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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