Water → 3-Iodo-5-nitro-1-trityl-1H-indazole

HRID 1610100Notes

Reaction equation

HRID 1610100 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1.[H-].[Na+].[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>O1CCCC1.C(OCC)(=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178526495HCID 178526495, compound

Product 1

HCID 222608163-Iodo-5-nitro-1-trityl-1H-indazoleYield 95.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 27.5 g of 3-iodo-5-nitro-1H-indazole in 300 ml tetrahydrofuran at 0° C. in an atmosphere of nitrogen gas was added 6.1 g of 60% sodium hydride, and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added 39.8 g of trityl chloride, followed by stirring at room temperature for 1 hour. Water was added 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 resulting crude crystals were washed with diethyl ether, to give 48.5 g of the title compound as colorless crystals.

Workup

  1. stirringby stirring at room temperature for 1 hour
  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. washThe resulting crude crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-a9838a8399f34b5f8aa72dd636381270
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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