Water → HCID 22260740, compound

HRID 1610129

Reaction equation

HRID 1610129 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][N:6]=[C:5]2[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1.[H-].[Na+].[Cl-].[C:22]1([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([C:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[N:6]=[C:5]2[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22260971Triphenylmethane chlorideHCID 178422425HCID 178422425, compound

Product 1

HCID 22260740HCID 22260740, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.56 g of 5-bromo-3-(3-fluorophenyl)-7-methyl-1H-indazole in 30 ml of dimethylformamide was added 0.50 g of sodium hydride at room temperature, and the mixture was stirred at the same temperature for 15 minutes. At the same temperature, 2.34 g of triphenylmethane chloride was added and the mixture was stirred at the same temperature for one day. Water was added to the reaction mixture and the mixture was diluted with ethyl acetate. The organic layer was sequentially washed with saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10) and the resulting crystals were washed with diethyl ether, to give 1.94 g of the title compound as colorless crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for one day
  2. washThe organic layer was sequentially washed with saturated aqueous ammonium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10)
  7. washthe resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-6435ab83239c442aa72212c21448c09f
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Linked notes

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