HCID 121386270, compound → HCID 83866933, compound

HRID 2202902Notes

Reaction equation

HRID 2202902 reaction equation
[CH3:1][Mg]Cl.[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([C:13](N(OC)C)=[O:14])[N:10]([CH3:19])[C:9]=2[CH:20]=1>C1COCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]=[C:11]([C:13](=[O:14])[CH3:1])[N:10]([CH3:19])[C:9]=2[CH:20]=1

Participants

4

Reactant 2

HCID 121386270HCID 121386270, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 83866933HCID 83866933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium chloride (1.0 M in THF, 4.70 ml) was added dropwise to a solution of 6-bromo-N-methoxy-N,1-dimethyl-1H-benzimidazole-2-carboxamide (700 mg) in THF (10 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 ao in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc), and the resulting solid was washed with IPE to give the title compound (360 mg) 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 ao in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)
  8. washthe resulting solid was washed with IPE

Sources & evidence

ORD record
ord-ca12004c823f411e9c36a5491d7da03a
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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