Phenylboronic Acid → 1-phenyl-1H-imidazo[4,5-c]pyridine

HRID 243039Notes

Reaction equation

HRID 243039 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:10]1([N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[N:3]=[CH:2]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:10]1([N:3]2[C:4]3[CH:5]=[N:6][CH:7]=[CH:8][C:9]=3[N:1]=[CH:2]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 178419860HCID 178419860, compound

Product 2

HCID 53284731-phenyl-1H-imidazo[4,5-c]pyridineHCID 681571853-phenyl-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

1H-Imidazo[4,5-c]pyridine (2.01 g, 0.0169 mol), copper acetate (7.66 g, 42.2 mmol) and phenyl boronic acid (5.14 g, 042.2 mmol) in pyridine (60 mL) were stirred vigorously at 37° C. in a flask open to the atmosphere for 3 days. The mixture was allowed to cool to RT then partitioned between water and DCM (3×50 mL). The combined DCM extracts were washed with water, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (SiO2 0-6% (2M ammonia in methanol) in DCM) to give 1-phenyl-1H-imidazo[4,5-c]pyridine (1.60 g) and 3-phenyl-3H-imidazo[4,5-c]pyridine (1.06 g) as white solids (combined 81%).

Workup

  1. customthen partitioned between water and DCM (3×50 mL)
  2. washThe combined DCM extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2 0-6% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record
ord-3da62fae71e1414da1a87a27fd0c36a8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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