Potassium Carbonate → 2-(5-bromo-pyridin-3-yl)-5-methoxy-1-methyl-1H-benzoimidazole

HRID 1048988Notes

Reaction equation

HRID 1048988 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:11])[C:6]([NH:9][CH3:10])=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=O)[CH:16]=[N:17][CH:18]=1.OOS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:12][C:13]1[CH:14]=[C:15]([C:19]2[N:9]([CH3:10])[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:11]=2)[CH:16]=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 45184444-methoxy-1-N-methylbenzene-1,2-diamineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 666927982-(5-bromo-pyridin-3-yl)-5-methoxy-1-methyl-1H-benzoimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxy-N1-methyl-benzene-1,2-diamine (34; 0.5 g, 0.00328 mol) and 5-bromo-pyridine-3-carbaldehyde (0.61 g, 0.00328 mol) in DMF (10 ml) and H2O (4 ml) was added OXONE® monopersulphate (2.42 g, 0.00394 mol). Reaction mass was stirred at room temperature for 3 h. The reaction mixture was basified with 10% K2CO3 solution to pH˜8-10 and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the crude compound which was purified by column chromatography to obtain title compound 2-(5-bromo-pyridin-3-yl)-5-methoxy-1-methyl-1H-benzoimidazole (35).

Workup

  1. customReaction mass
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto afford the crude compound which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9fc78bd795cc47be94b4ece473104db2
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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