Dimethyl Sulfate → 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole

HRID 902536Notes

Reaction equation

HRID 902536 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][N:15]=[CH:14]2.S(OC)(O[CH3:22])(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[C:13](=[CH:14][N:15]([CH3:22])[N:16]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 686153577-(2,4-dichloro-phenyl)-1H-indazole

Product 1

HCID 115297297-(2,4-dichloro-phenyl)-2-methyl-2H-indazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 7-(2,4-dichloro-phenyl)-1H-indazole (4; 1.12 g, 4.27 mmol) and dimethyl sulfate (0.405 mL, 4.28 mmol) in 15 mL of toluene was stirred at 110° C. for 17 h, allowed to cool, then chilled at 0-5° C. The mixture was carefully washed with 15 mL of a saturated aqueous NaHCO3 solution, dried over MgSO4, filtered (rinsing with diethyl ether), and concentrated to an orange oil Column chromatography (0→33% EtOAc/hexanes) afforded 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole as a viscous yellow oil (5; 0.92 g, 78%).

Workup

  1. temperatureto cool
  2. washThe mixture was carefully washed with 15 mL of a saturated aqueous NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. wash(rinsing with diethyl ether)
  6. concentrationconcentrated to an orange oil Column chromatography (0→33% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9c6f5532e96244498f871eac27bc7208
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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