Trimethylsilyldiazomethane → methyl 4-(4-bromo-1H-imidazol-1-yl)-3-methoxybenzoate

HRID 71196Notes

Reaction equation

HRID 71196 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[O:16][CH3:17])[CH:6]=1.[CH3:18][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:18])=[O:12])=[CH:9][C:8]=2[O:16][CH3:17])[CH:6]=1

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 666082014-(4-bromo-1H-imidazol-1-yl)-3-methoxybenzoic acid

Product 1

HCID 66607935methyl 4-(4-bromo-1H-imidazol-1-yl)-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 4-(4-bromo-1H-imidazol-1-yl)-3-methoxybenzoic acid (1.90 g) in toluene (20 mL) and methanol (5 mL) was added trimethylsilyldiazomethane (2M hexane solution, 3.84 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added trimethylsilyldiazomethane (2M hexane solution, 0.96 mL), the mixture was stirred for 1 hr, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to give the title compound (1.32 g).

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-98485e7650d047398aeb8f7445f6a946
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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