Trityl chloride → 3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile

HRID 34067Notes

Reaction equation

HRID 34067 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:22](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([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>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4]([C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 178509418HCID 178509418, compound

Product 1

HCID 689267013-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carbonitrileYield 47.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.8 g of 3-iodo-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile in 70 mL of dichloromethane were added 13.1 mL of diisopropylethylamine, 2.4 g of tetra-n-butylammonium iodide and 12.0 g of trityl chloride at room temperature, and stirred at this temperature for a day. The solution was evaporated, diluted with ethyl acetate, washed successively with saturated ammonium chloride and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10), to afford 5.2 g of the title compound as colorless crystals.

Workup

  1. customThe solution was evaporated
  2. additiondiluted with ethyl acetate
  3. washwashed successively with saturated ammonium chloride and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-ece1696588f2407289d727effe25fd70
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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