Tetramethyltin → HCID 178430477, compound

HRID 2304705Notes

Reaction equation

HRID 2304705 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.[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>[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 (11) 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 (NH, 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 (NH, sat'd 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-ed0ed940e0bf4858af6681e59f7309a2
Source dataset
uspto-grants-2002_08
Patent number
US06436982B1

Reaction notes

Loading…