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

HRID 2304748Notes

Reaction equation

HRID 2304748 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]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=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 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

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-e4ab0645ddb7498cb398c74f0f9d61bd
Source dataset
uspto-grants-2002_08
Patent number
US06436982B1

Reaction notes

Loading…