Selectfluor → HCID 178526427, compound

HRID 520570Notes

Reaction equation

HRID 520570 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

Conditions

Temperature
100 °C

Procedure

To a solution of 6-bromo-4-nitro-1H-indazole (5 g) in acetonitrile (50 ml) and acetic acid (10 ml) was added Selectfluor (9.39 g). The resulting mixture was heated to 100° C. and stirred for two days. The reaction mixture was concentrated under vacuum. The residue was dissolved in DCM and then filtered off. The sample was absorbed onto silica powder then solid loaded onto the companion where it was purified on a 120 g silica column using a 0-100% ethyl acetate:cyclohexane gradient. The appropriate fractions were combined and concentrated to yield the title compound as an orange solid, 2 g.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in DCM
  3. filtrationfiltered off
  4. customThe sample was absorbed onto silica powder
  5. customwas purified on a 120 g silica column
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d3a1492b7bc947e9896a67d40edb8d5d
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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