Potassium Carbonate → HCID 18957890, compound

HRID 2379129Notes

Reaction equation

HRID 2379129 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.Br[C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu]>[C:13]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=[C:11]([N:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[N:1]=[CH:2]2)[CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 164493-BromobiphenylHCID 67504Imidazo(4,5-b)pyridine

Product 1

HCID 18957890HCID 18957890, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of imidazo[4,5-b]pyridine (595 mg, 5 mmol), 3-bromobiphenyl (1.16 g, 5 mmol), potassium carbonate (1.03 g, 7.5 mmol), and copper powder (2.0 g) in N-methylpyrrolidone (10 ml) was heated to 200° under nitrogen for 4 h. After dilution with ethyl acetate the mixture was filtered through celite. Water was added and the phases were separated. After two more extractions with ethyl acetate the combined organic phases were dried and evaporated to give a light brown oil. Column chromatography on silica gel gave the two products as separate fractions with 1-(3biphenylyl)imidazo[4,5-b]pyridine being the more polar one. This product was precipitated as the oxalate. Yield: 100 mg, 0.3 mmol, 5%. mp 174°-176° C. Yield of 3(3-biphenylyl)imidazo[5,4-b]pyridine: 270 mg, 1 mmol, 20%. mp 89°-91° C.

Workup

  1. temperaturewas heated to 200° under nitrogen for 4 h
  2. filtrationAfter dilution with ethyl acetate the mixture was filtered through celite
  3. additionWater was added
  4. customthe phases were separated
  5. extractionAfter two more extractions with ethyl acetate the combined organic phases
  6. customwere dried
  7. customevaporated
  8. customto give a light brown oil
  9. customColumn chromatography on silica gel gave the two products
  10. customas separate fractions with 1-(3biphenylyl)imidazo[4,5-b]pyridine being the more polar one
  11. customThis product was precipitated as the oxalate

Sources & evidence

ORD record
ord-62ea4da1f94c45eb90adfabd92220b68
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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