Triethylamine → 1-(methylsulfonyl)-5-nitro-1H-indazole

HRID 1269879Notes

Reaction equation

HRID 1269879 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)([O-:8])=[O:7].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][S:2]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:17][CH:16]=2)[CH:12]=[N:13]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 215015-NitroindazoleHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium Bicarbonate

Product 1

HCID 229340351-(methylsulfonyl)-5-nitro-1H-indazoleYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (887 μl, 7.20 mmol) was added to a suspension of 5-nitroindazole (979 mg, 6.00 mmol) and triethylamine (2.0 ml, 14.3 mmol) in dichloromethane (20 ml) at 0° C., and the resulting mixture was stirred at room temperature for 3 hours. Methanesulfonyl chloride (222 μl, 1.80 mmol) was further added thereto, followed by stirring for another 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution to terminate the reaction, followed by extraction with chloroform. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by washing with methanol to obtain 1-(methylsulfonyl)-5-nitro-1H-indazole (1.16 g, 80%).

Workup

  1. stirringby stirring for another 1 hour
  2. customto terminate
  3. customthe reaction
  4. extractionfollowed by extraction with chloroform
  5. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified
  10. washby washing with methanol

Sources & evidence

ORD record
ord-a5d2277c7a6742ec978a0bcf6023766e
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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