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

HRID 924563

Reaction equation

HRID 924563 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-be958e33360f48408f705ba26fcb999f
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Linked notes

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