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

HRID 924563

반응식

HRID 924563 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-be958e33360f48408f705ba26fcb999f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09281483B2

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