Tetramethyltin → HCID 178430477, compound

HRID 429547Notes

Reaction equation

HRID 429547 reaction equation
Br[C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11].[CH3:12][Sn](C)(C)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:12][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 178507337HCID 178507337, compound

Product 1

HCID 178430477HCID 178430477, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

A solution of 4-bromo-5-aminobenzimidazole (180 mg, 0.84 mmol), tetramethyltin (330 mg, 2.4 mmol) and bis(triphenylphosphine)palladium (II) chloride (20 mg) in 5 ml of anhydrous DMF was placed in sealed tube and stirred for 12 h at 145° C. The reaction mixture was concentrated in vacuo, yielding an oily residue which was subjected to column chromatographic separation (NH3 sat'd 10% MeOH/EtOAc) to yield 140 mg (0.83 mmol, >95 %) of 4-methyl-5-aminobenzimidazole.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customyielding an oily residue which
  3. customwas subjected to column chromatographic separation (NH3 sat'd 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-5b21f4909d8f48d8928093ec4c2daa11
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

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