Trityl chloride → HCID 22260730, compound

HRID 1610146Notes

Reaction equation

HRID 1610146 reaction equation
[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.[H-].[Na+].[C:22]1([C:28](Cl)([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.[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[CH:9][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:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22261064HCID 22261064, compound

Product 1

HCID 22260730HCID 22260730, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A total of 530 mg of 5-bromo-3-(3-fluoro-phenyl)-4-methoxy-1H-indazole obtained in Production Example II-2-c was dissolved in 8.3 ml of dimethylformamide, and 99 mg of sodium hydride (60% content) was added under ice-cooling and stirring. After stirring for 15 minutes, 483 mg of triphenylmethyl chloride was added. After stirring at room temperature for 1 hour, saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:8), to give 998 mg of the title compound as pale yellow crystals.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 15 minutes
  3. stirringAfter stirring at room temperature for 1 hour
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe crude product was purified
  9. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:8)

Sources & evidence

ORD record
ord-3a221412fbc6414b9bb8f5f07f821484
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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