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

HRID 341229

반응식

HRID 341229 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 68594318Toluene-methanol ethanol water용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-965f4eff0732487dbdf7d17a47502445
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895745B2

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