HCID 121386270, compound → HCID 121386244, compound

HRID 2202871Notes

Reaction equation

HRID 2202871 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13]([C:15](N(OC)C)=[O:16])[N:12]([CH3:21])[C:11]=2[CH:22]=1>C1COCC1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13]([C:15]([CH:1]3[CH2:2][CH2:3]3)=[O:16])[N:12]([CH3:21])[C:11]=2[CH:22]=1

Participants

4

Reactant 2

HCID 121386270HCID 121386270, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 121386244HCID 121386244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopropylmagnesium bromide (0.70 M in THF, 7.19 ml) was added dropwise to a solution of 6-bromo-N-methoxy-N,1-dimethyl-1H-benzimidazole-2-carboxamide (1.00 g) in THF (3 ml) at 0° C. The mixture was stirred at 0° C. under Ar atmosphere for 30 min. The mixture was quenched with saturated NH4Cl solution and extracted with EtOAc twice. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc), and the resulting solid was washed with hexane to give the title compound (0.625 g) as a white solid.

Workup

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc twice
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)
  8. washthe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-cca85b674ab645fc80db619fd4ed6a12
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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