Chloroform → 4-Bromo-7-methyl-5-aminobenzimidazole

HRID 2299165Notes

Reaction equation

HRID 2299165 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[C:5](Br)=[CH:4][C:3]=1[NH2:12].[CH3:13][Sn](C)(C)C.[CH:18](Cl)(Cl)Cl.C[N:23]([CH:25]=O)[CH3:24]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[C:5]([CH3:13])=[CH:4][C:3]=1[NH2:12].[CH3:18][C:2]1[C:3]2[NH:12][CH:25]=[N:23][C:24]=2[C:5]([CH3:4])=[CH:6][C:10]=1[NH2:9]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 11661TetramethyltinHCID 183798914,7-Dibromo-5-aminobenzimidazole

Product 2

HCID 183798334-Bromo-7-methyl-5-aminobenzimidazoleYield 29%HCID 183798614,7-dimethyl-3H-benzimidazol-5-amine

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

A solution of 4,7-dibromo-5-aminobenzimidazole (1.5 g, 5.1 mmol) in 10 ml of DMF was transferred into pressure bottle under Ar2. To the solution was added tetramethyltin (3.6 ml, 20 mmol). and bis(triphenylphosphine)palladium(II) chloride (200 mg). The resulting reaction mixture was stirred at 140° C. for 24 h and concentrated in vacuo, yielding a dark oil which was subjected to column chromatography (40% EtOAC/CHCl3) to yield 0.34 g (1.5 mmol, 29%) of the desired product as well as 0.75 g of 4,7-dimethyl-5-aminobenzimidazole.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customyielding a dark oil which

Sources & evidence

ORD record
ord-89d589deb21346a5b9fef6bd37703ebe
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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