4-Toluenesulfonyl chloride → 10-[(4-methylphenyl)sulfonyl]-10H-pyrazolo[1',5':1,2]imidazo[4,5-c]quinoline

HRID 415545Notes

Reaction equation

HRID 415545 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:13]3[NH:14][CH:15]=[CH:16][C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.[H-].[Na+].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O1CCCC1.C(OC)(C)(C)C>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:14]2[N:13]3[C:3]4[C:2]5[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=5)[N:6]=[CH:5][C:4]=4[N:11]=[C:12]3[CH:16]=[CH:15]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 6661988810H-pyrazolo[1',5':1,2]imidazo[4,5-c]quinoline

Product 1

HCID 6662030510-[(4-methylphenyl)sulfonyl]-10H-pyrazolo[1',5':1,2]imidazo[4,5-c]quinolineYield 28.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 10H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]quinoline (1.00 g, 4.80 mmol) in tetrahydrofuran (24 mL), under a nitrogen atmosphere, was chilled in an ice-water bath. The solution was treated with NaH (0.29 g, 7.20 mmol, 60%) in small portions over 2 min. After 10 min, the mixture was treated with p-toluenesulfonyl chloride (1.01 g, 5.28 mmol), and allowed to come to ambient temperature. After 1.5 h the reaction was quenched with slow addition of water (5 mL). The reaction mixture was concentrated under reduced pressure to yield a brown solid. The solid was purified by prep. HPLC (100 g silica gel eluted with 1-10% CMA in chloroform) to give a tan foam. The foam was dissolved in methyl tert-butyl ether (25 mL) and filtered through filter paper. The filtrate was concentrated under reduced pressure to yield 0.49 g of 10-[(4-methylphenyl)sulfonyl]-10H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]quinoline as a tan solid.

Workup

  1. customto come to ambient temperature
  2. customAfter 1.5 h the reaction was quenched with slow addition of water (5 mL)
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto yield a brown solid
  5. customThe solid was purified by prep
  6. washHPLC (100 g silica gel eluted with 1-10% CMA in chloroform)
  7. customto give a tan foam
  8. filtrationfiltered
  9. filtrationthrough filter paper
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f22c53081e542da8b9952d8290ac9b9
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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