Water → 5-Bromo-6-fluoro-3-iodo-1-trityl-1H-indazole

HRID 34130

Reaction equation

HRID 34130 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]=[C:5]2[I:12].[H-].[Na+].[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.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])[N:7]([C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[N:6]=[C:5]2[I:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178505409HCID 178505409, compound

Product 1

HCID 689307235-Bromo-6-fluoro-3-iodo-1-trityl-1H-indazoleYield 73.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.0 g of 5-bromo-6-fluoro-3-iodo-1H-indazole in N,N-dimethylformamide in 150 mL was added 0.42 g of sodium hydride at room temperature, and the resultant solution was stirred for 15 minutes, added with 2.45 g of trityl-chloride, and stirred at this temperature for 1 hour. After adding water and diluting with ethyl acetate, washing successively with aqueous ammonium chloride and saturated brine and drying over anhydrous magnesium sulfate, the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:30-1:5), and the resultant product was added with n-hexane. Then the precipitated crystals were washed with diethyl ether:n-hexane=1:10, to afford 3.79 g of the title compound as colorless crystals.

Workup

  1. washwashing successively with aqueous ammonium chloride and saturated brine
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:30-1:5)
  6. additionthe resultant product was added with n-hexane
  7. washThen the precipitated crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-b36d63a95e0e48d082f464e0c9f219c6
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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