4-Toluenesulfonyl chloride → cyclopropyl(1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-yl)methanone

HRID 1943924Notes

Reaction equation

HRID 1943924 reaction equation
[H-].[Na+].[CH:3]1([C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)=[O:7])[CH2:5][CH2:4]1.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>CN(C=O)C>[CH:3]1([C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[N:9]=2)=[O:7])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178520051HCID 178520051, compound

Product 1

HCID 67089081cyclopropyl(1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-yl)methanoneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.030 g, 0.75 mmol) was added to cyclopropyl(1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (100 mg, 0.534 mmol) in DMF (2 mL) at 0° C. After 10 minutes, tosyl chloride (0.13 g, 0.69 mmol) was added, and the reaction mixture was allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 16 hours and then quenched with ice and water. The mixture was extracted with EtOAc (3×10 mL) and dried over sodium sulfate. Column chromatography afforded cyclopropyl(1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (127 mg, 70%) as an oil, which crystallized upon standing.

Workup

  1. customquenched with ice and water
  2. extractionThe mixture was extracted with EtOAc (3×10 mL)
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-d2b31378fc4748aa9c11fdb52fb6f75c
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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