N-Iodosuccinimide → HCID 178505409, compound

HRID 34129Notes

Reaction equation

HRID 34129 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][N:6]=[CH:5]2.[I:12]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][N:6]=[C:5]2[I:12]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 468639235-Bromo-6-fluoro-1H-indazole

Product 1

HCID 178505409HCID 178505409, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 10.0 g of 5-bromo-6-fluoro-1H-indazole in 150 mL of N,N-dimethylformamide was added 10.5 g of N-iodosuccinimide at room temperature, and stirred at 70° C. for 2 days. Then the solution was diluted with ethyl acetate, washed successively with aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crystals precipitated by adding diethyl ether to the residue were collected by filtration. The filtrate was further concentrated and purified and separated by silica gel column chromatographsy (ethyl acetate:n-hexane=1:10-1:5) and combined with the previous crystals, to afford 14.5 g of the title compound as colorless crystals.

Workup

  1. washwashed successively with aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe crystals precipitated
  5. additionby adding diethyl ether to the residue
  6. filtrationwere collected by filtration
  7. concentrationThe filtrate was further concentrated
  8. custompurified
  9. customseparated by silica gel column chromatographsy (ethyl acetate:n-hexane=1:10-1:5)

Sources & evidence

ORD record
ord-a8cb828c57634091a7280e761e4badb3
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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