3-Nitropyridin-2-ylamine → 2-(4-Fluorophenyl)-8-nitroimidazo[1,2-a]pyridine

HRID 456683

반응식

HRID 456683 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=O>CN(C)C=O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[N:1]=[C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]3[CH:12]=2)=[CH:16][CH:17]=1

참가 물질

4

반응물 2

HCID 778873-Nitropyridin-2-ylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

생성물 1

HCID 179762862-(4-Fluorophenyl)-8-nitroimidazo[1,2-a]pyridine수율 36.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-amino-3-nitropyridine (1.3 g, 9.3 mmol) in N,N-dimethylformamide (20 mL) was added 2-bromo-4′-fluoroacetophenone (2 g, 9.3 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 dichloromethane and the organic phase was washed with aqueous sodium bicarbonate 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 methanol to give 870 mg (36%) of 2-(4-fluorophenyl)-8-nitroimidazo[1,2-α]pyridine as a brown solid. 1H NMR (d6-DMSO): δ 8.98 (d, 1H), 8.69 (s,1H), 8.32 (d, 1H), 8.10 (q, 2H), 7.36 (t, 2H), 7.15 (t, 1H); 19F NMR (DMSO-d6) δ −113.7; MS m/z 258 (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 dichloromethane
  5. washthe organic phase was washed with aqueous sodium bicarbonate
  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 methanol

출처 및 근거

ORD 기록
ord-55a334e591de4e1187675bab72ccfefd
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186714B2

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