Azobisisobutyronitrile → HCID 66765793, compound

HRID 402817Notes

Reaction equation

HRID 402817 reaction equation
C(N1C2C(=CC(Cl)=C(F)C=2)C(C)=N1)(C)(C)C.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N(Br)C(=O)C1.[C:37]([N:41]1[C:49]2[C:44](=[CH:45][C:46]([Cl:51])=[C:47]([F:50])[CH:48]=2)[C:43]([CH:52](Br)[Br:53])=[N:42]1)([CH3:40])([CH3:39])[CH3:38]>ClC(Cl)C>[Br:53][CH2:52][C:43]1[C:44]2[C:49](=[CH:48][C:47]([F:50])=[C:46]([Cl:51])[CH:45]=2)[N:41]([C:37]([CH3:40])([CH3:39])[CH3:38])[N:42]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68093301HCID 68093301, compoundHCID 86685272HCID 86685272, compound

Product 1

HCID 66765793HCID 66765793, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To 1-tert-butyl-5-chloro-6-fluoro-3-methyl-1H-indazole (153 mg, 0.636 mmol) in dichloroethane (3.0 mL) were added AIBN (20.88 mg, 0.127 mmol) and NBS (124 mg, 0.699 mmol) and the reaction mixture was refluxed under a sunlamp for 3 hours. The reaction was cooled to room temperature and after filtering through a pad of celite, the solution was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (2×15 mL) and water (10 mL), washed with saturated sodium bicarbonate (15 mL), brine (10 mL) and dried over sodium sulfate. The solution was filtered and concentrated under reduced pressure to give a mixture of the title compound and 1-tert-butyl-5-chloro-3-(dibromomethyl)-6-fluoro-1H-indazole (168 mg).

Workup

  1. temperaturethe reaction mixture was refluxed under a sunlamp for 3 hours
  2. filtrationafter filtering through a pad of celite
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate (2×15 mL) and water (10 mL)
  5. washwashed with saturated sodium bicarbonate (15 mL), brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated under reduced pressure
  9. customto give

Sources & evidence

ORD record
ord-5a1594a48bd54e7eb0b96d714bae3332
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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