Acetyl chloride → 10-Fluoro-imidazo[1,2-f]phenanthridine

HRID 1097141

반응식

HRID 1097141 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[C:13]1[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]1)=[N:7][C:6]=2[NH2:16].[C:17](Cl)(=O)[CH3:18].C(=O)(O)[O-].[Na+]>O.C(O)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:7]([CH:17]=[CH:18][N:16]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH:15]=1

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 112528289-Fluoro-6-phenanthridinamine

생성물 1

HCID 5816243310-Fluoro-imidazo[1,2-f]phenanthridine수율 52%

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

9-Fluoro-6-Phenanthridinamine (0.8 g, 3.7 mmol), and a 50% solution of acetyl chloride (0.4 g, 5.66 mmol) in water containing sodium bicarbonate (0.6 g, 7.54 mmol) was dissolved in isopropyl alcohol (25 mL). The reaction mixture was refluxed for 17 hours under a nitrogen pad. The reaction mixture was cooled to room temperature and the precipitate vacuum filtered and washed with methylene chloride. The crude product was purified by column chromatography using a 1:1 ratio of ethyl acetate and hexanes as the eluants followed by distillation to give 10-fluoro-imidazo[1,2-f]phenanthridine) (0.46 g, 52% yield).

후처리

  1. temperatureThe reaction mixture was refluxed for 17 hours under a nitrogen pad
  2. filtrationthe precipitate vacuum filtered
  3. washwashed with methylene chloride
  4. customThe crude product was purified by column chromatography
  5. distillationfollowed by distillation

출처 및 근거

ORD 기록
ord-21f04cb5255648949330893b1393cd3c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08142909B2

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