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

HRID 2186114Notes

Reaction equation

HRID 2186114 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 290%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, 290%) 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-cb28f360f8744dd38a64e8533f81ceb4
Source dataset
uspto-grants-2002_06
Patent number
US06403626B1

Reaction notes

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