Acetic Anhydride → 2-Methylpropyl 5-bromo-4-fluoro-2-methyl-1H-benzimidazole-1-carboxylate

HRID 241029Notes

Reaction equation

HRID 241029 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:11](OC(=O)C)(=O)[CH3:12].Cl[C:19]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:20]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:19]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:20])[C:11]([CH3:12])=[N:9][C:4]=2[C:3]=1[F:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 62365Isobutyl chloroformateHCID 27832034-Bromo-3-fluorobenzene-1,2-diamine

Product 1

HCID 687771362-Methylpropyl 5-bromo-4-fluoro-2-methyl-1H-benzimidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the method of reagent preparation 19 using 5 4-bromo-3-fluorobenzene-1,2-diamine and acetylation with acetic anhydride in tetrahydrofurane in step 1 then treatment with isobutyl chloroformate in step 3. MS (EI) for C13H14BrN2O2: 328, 330 (MH+, Br isotope pattern).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-021d83c5fbf44ad4bd64e1e375e77f4e
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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