2-Bromo-1-(4-fluorophenyl)ethan-1-one → 8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine

HRID 456689

반응식

HRID 456689 반응식
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=O.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:8][C:7]1[C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:1]=2)[CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 6932672-Amino-3-chloropyridine

생성물 1

HCID 179762858-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine수율 80.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-amino-3-chloropyridine (6.51 g, 51 mmol) and 2-bromo-4′-fluoroacetophenone (13.0 g, 60 mmol) in ethanol (100 mL) was added sodium bicarbonate (4.91 g, 60 mmol) and the reaction mixture was heated at reflux for 6 hours. The resulting mixture was concentrated to a solid in vacuo. This residue was dissolved in ethyl acetate and the organic phase was washed with water and an aqueous sodium chloride solution. The organic phase was dried (magnesium sulfate), filtered through a silica gel pad and concentrated to give a solid. This solid was recrystallized from acetonitrile, to give 10.1 g (80%) 8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridine as a solid. 1H NMR (CDCl3): δ 8.06 (d, 1H), 7.96 (q, 2H), 7.86 (s, 1H), 7.25 (d, 1H), 7.13 (t, 2H), 6.73 (t, 1H); 19F NMR (CDCl3) δ −114.0; MS m/z 247 (M+1).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe resulting mixture was concentrated to a solid in vacuo
  4. dissolutionThis residue was dissolved in ethyl acetate
  5. washthe organic phase was washed with water
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. filtrationfiltered through a silica gel pad
  8. concentrationconcentrated
  9. customto give a solid
  10. customThis solid was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-33ba5224952445338ce4fa3525dc4b22
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186714B2

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