Dimethylformamide → HCID 178428481, compound

HRID 2299158Notes

Reaction equation

HRID 2299158 reaction equation
Br[C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1.[CH3:12]N(C=O)C.C[Sn](C)(C)C>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.CO.C(Cl)(Cl)Cl>[CH3:12][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11661TetramethyltinHCID 178507224HCID 178507224, compound

Product 1

HCID 178428481HCID 178428481, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
140 °C

Procedure

To the solution of 4-bromo-6-aminobenzimidazole (0.85 g, 6.0 mmol) in sealed tube with 10 ml of DMF was added tetramethyltin (1.7 ml, 12 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.20 g). The resulting reaction mixture was stirred for 12 h at 140° C. and concentrated in vacuo, yielding oily residue which was subjected to column chromatography (5% MeOH/CHCl3)to produce 0.28 g (45%) of the desired product.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customyielding oily residue which

Sources & evidence

ORD record
ord-a4ad0e2458af4d41979480319e6f2b27
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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