Selectfluor → HCID 178526427, compound

HRID 244698Notes

Reaction equation

HRID 244698 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[B-](F)(F)(F)[F:15].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:15])=[N:7][NH:8]2)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 247280596-bromo-4-nitro-1H-indazole

Product 1

HCID 178526427HCID 178526427, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-bromo-4-nitro-1H-indazole (10 g, 41.3 mmol, available from Sinova) in acetonitrile (100 ml) and acetic acid (20.00 ml) was added Selectfluor® (22.10 g, 83 mmol). The resultant mixture was heated to 100° C. and stirred overnight. The resultant orange solution was concentrated under vacuum then partitioned between ethyl acetate and water. The layers were separated and the aqueous extracted again with ethyl acetate. The combined organics were dried over MgSO4, filtered and concentrated. The solid was then dissolved in 20 ml DCM, loaded onto a 330 g silica column and purified on a 0-100% EtOAc/Cyclohexane gradient. The relevant fractions were combined and concentrated to yield the title compound as an orange solid (6.9 g).

Workup

  1. concentrationThe resultant orange solution was concentrated under vacuum
  2. customthen partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. extractionthe aqueous extracted again with ethyl acetate
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe solid was then dissolved in 20 ml DCM
  9. custompurified on a 0-100% EtOAc/Cyclohexane gradient
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a42417ba76df47ddaf73c0ea41735ab6
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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