Trityl chloride → 6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

HRID 588084Notes

Reaction equation

HRID 588084 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9](=[O:12])[NH:10][NH:11][C:4]=2[CH:3]=1.[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.[H-].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9](=[O:12])[NH:10][N:11]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 826552466-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

Product 1

HCID 1182721366-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (3.1 g, 16.85 mmol) and trityl chloride (4.93 g, 17.69 mmol) in DMF (50 mL) was charged with sodium hydride (60% in mineral oil, 1.011 g, 25.3 mmol) and stirred at room temperature for 1.5 h. The reaction mixture was poured into sat. aq. NaHCO3 and extracted with Et2O (×3). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (0-50% EtOAc/DCM) to provide 6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one. MS ESI calc'd. for C26H20ClN3O [M+1]+ 426. found 426.

Workup

  1. extractionextracted with Et2O (×3)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0-50% EtOAc/DCM)

Sources & evidence

ORD record
ord-7dbdd65de1e04655931fa830b5eca25c
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…