Potassium Carbonate → 7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridine

HRID 341229

Reaction equation

HRID 341229 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CO)=CC=CC=1.C(O)C.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][N:5]3[CH:8]=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 196959017-Chloroimidazo(1,2-a)pyridine

Product 1

HCID 593207997-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridineYield 83%

Reagents, catalysts & solvents 1

HCID 68594318Toluene-methanol ethanol waterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-chloro-imidazo[1,2-a]pyridine (15.0 g, 98.6 mmol), 4-fluorophenylboronic acid (16.55 g, 118.3 mmol), potassium carbonate (81.5 g, 590 mmol) in toluene-methanol-ethanol-water (1:1:1:1, 800 mL) was degassed with N2 and then bis(tri-tert-butylphosphine)palladium(0) (400 mg) added. The mixture was degassed and then heated to 80° C. for 18 h. The mixture was cooled to ambient, transferred to a separating funnel and the layers separated. The organic portion was reduced under reduced pressure and the residue extracted with dichloromethane. The dichloromethane extracts were washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to afford 17.3 g (83%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.22 (1H, d), 7.87 (1H, s), 7.71 (1H, s), 7.69-7.58 (3H, m), 7.20 (2H, t), 7.11 (1H, d).

Workup

  1. customwas degassed with N2
  2. additionbis(tri-tert-butylphosphine)palladium(0) (400 mg) added
  3. customThe mixture was degassed
  4. temperatureThe mixture was cooled
  5. customtransferred to a separating funnel
  6. customthe layers separated
  7. extractionthe residue extracted with dichloromethane
  8. washThe dichloromethane extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-965f4eff0732487dbdf7d17a47502445
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Linked notes

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