Trityl chloride → 3-Bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 34084Notes

Reaction equation

HRID 34084 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][N:3]=1.[H-].[Na+].[C:13](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.ClCCl>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178419485HCID 178419485, compound

Product 1

HCID 689284263-Bromo-1-trityl-1H-pyrazolo[4,3-c]pyridineYield 50.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.69 g of 3-bromo-1H-pyrazolo[4,3-c]pyridine in 72 mL of dimethylformamide was added 1.42 g of sodium hydride at room temperature and stirred for 15 minutes, and then added with 6.6 g of trityl chloride and stirred at this temperature for a day. The solution was diluted with dichloromethane, and the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The precipitated crystals were washed with ethyl acetate, the filtrate was evaporated, and the residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:3), an the resultant product was combined with the above crystals, to afford 5.28 g of the title compound as colorless crystals.

Workup

  1. stirringstirred at this temperature for a day
  2. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. washThe precipitated crystals were washed with ethyl acetate
  6. customthe filtrate was evaporated
  7. customthe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:3)

Sources & evidence

ORD record
ord-94472c5a89c94cfe856eb65738c5d852
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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