HCID 121386270, compound → HCID 89691245, compound

HRID 2203035Notes

Reaction equation

HRID 2203035 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([C:14](N(OC)C)=[O:15])[N:11]([CH3:20])[C:10]=2[CH:21]=1>C1COCC1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([C:14](=[O:15])[CH2:1][CH3:2])[N:11]([CH3:20])[C:10]=2[CH:21]=1

Participants

4

Reactant 2

HCID 121386270HCID 121386270, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 89691245HCID 89691245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethylmagnesium bromide (1 M in THF, 11.0 ml) was added to a solution of 6-bromo-N-methoxy-N,1-dimethyl-1H-benzo[d]imidazole-2-carboxamide (1.09 g) in THF (15 ml) at 0° C. The mixture was stirred at 0° C. under N2 atmosphere for 2 h. The mixture was quenched with saturated NH4Cl solution, and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (hexane/EtOAc) to give the title compound (0.86 g) as a white solid.

Workup

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  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 column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-12aa380fa41343deb67c9a1e5eb58271
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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