Phenyl chloroformate → 1-Benzenesulfonyl-3-(1-phenoxycarbonyl4-piperazinyl)-1H-indazole

HRID 1451007Notes

Reaction equation

HRID 1451007 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22](C)[CH2:21][CH2:20]3)=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22]([C:27]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:28])[CH2:21][CH2:20]3)=[N:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 148234251-(Benzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indazole

Product 1

HCID 184672231-Benzenesulfonyl-3-(1-phenoxycarbonyl4-piperazinyl)-1H-indazoleYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzenesulfonyl-3-(1-methyl-4-piperazinyl)-1H-indazole (2.1 g, 5.89 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.8 ml, 29.45 mmol) at room temperature. The reaction mixture was warmed to reflux for 2 hours, cooled to room temperature, and concentrated. The residue was diluted with ethyl acetate, filtered and purified via flash column chromatography (silica gel, ethyl acetate). Concentration of the product containing fractions gave an oil which solidified on standing. The product was washed well with heptane to give 1.5 g of a white solid, m.p. 112°-114° C.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with ethyl acetate
  5. filtrationfiltered
  6. custompurified via flash column chromatography (silica gel, ethyl acetate)
  7. additionConcentration of the product containing fractions
  8. customgave an oil which
  9. washThe product was washed well with heptane

Sources & evidence

ORD record
ord-664e40ab7fc4463b97583976a0f98af1
Source dataset
uspto-grants-1997_02
Patent number
US05602158

Reaction notes

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