Benzoyl Peroxide → HCID 22025334, compound

HRID 1792838Notes

Reaction equation

HRID 1792838 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH3:22])[CH:15]=[C:16]([Cl:21])[C:17]=3[O:19][CH3:20])[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH2:22][Br:23])[CH:15]=[C:16]([Cl:21])[C:17]=3[O:19][CH3:20])[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22025326HCID 22025326, compound

Product 1

HCID 22025334HCID 22025334, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-Benzenesulfonyl-6-chloro-7-methoxy-4-methyl-1H-indazole (2.45 g, 7.3 mmol), recrystallized N-bromosuccinimide (1.36 g, 7.6 mmol) and benzoyl peroxide (90 mg, 0.37 mmol) are dissolved in carbon tetrachloride (25 mL). The reaction is degassed and then placed in a 80° C. bath. The reaction is heated (about 2 h) until no starting material remains by TLC analysis (PhMe). The reaction is cooled, diluted with EtOAc, and washed with water. The solution is dried with MgSO4, concentrated and purified by column chromatography (silica, PhMe) to provide 1-benzenesulfonyl-4-bromomethyl-6-chloro-7-methoxy-1H-indazole.

Workup

  1. customThe reaction is degassed
  2. customplaced in a 80° C.
  3. temperatureThe reaction is heated (about 2 h) until no starting material remains by TLC analysis (PhMe)
  4. temperatureThe reaction is cooled
  5. additiondiluted with EtOAc
  6. washwashed with water
  7. dry with materialThe solution is dried with MgSO4
  8. concentrationconcentrated
  9. custompurified by column chromatography (silica, PhMe)

Sources & evidence

ORD record
ord-efa69b70099d4206978f2bc3d9f4c70b
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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