Phenyl chloroformate → HCID 18467270, compound

HRID 2394765Notes

Reaction equation

HRID 2394765 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[C:11]([CH:19]2[CH2:24][CH2:23][N:22](C)[CH2:21][CH2:20]2)=[N:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[C:11]([CH:19]2[CH2:24][CH2:23][N:22]([C:27]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])[CH2:21][CH2:20]2)=[N:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 140325551-benzoyl-6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole

Product 1

HCID 18467270HCID 18467270, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzoyl-6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole (2.0 g, 5.93 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.9 ml, 29.65 mmol) at room temperature. The reaction mixture was stirred at room temperature for 24 hours, refluxed for an additional 0.5 hours and subsequently concentrated. The remaining residue was dissolved into dichloromethane and washed with 10% HCl (aq.). The organic phase was dried (MgSO4), filtered, and concentrated to give an oil which was purified via flash column chromatography (silica gel, 20% DCM/EtOAc). Concentration of the product-containing fractions gave an oil which solidified on standing. The white solid was washed with EtOAc, leaving 0.47 g of the desired product, m.p. 137°-139° C.

Workup

  1. temperaturerefluxed for an additional 0.5 hours
  2. concentrationsubsequently concentrated
  3. dissolutionThe remaining residue was dissolved into dichloromethane
  4. washwashed with 10% HCl (aq.)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil which
  9. customwas purified via flash column chromatography (silica gel, 20% DCM/EtOAc)
  10. customConcentration of the product-containing fractions gave an oil which
  11. washThe white solid was washed with EtOAc

Sources & evidence

ORD record
ord-63bb2428e66a4d92a2020542386f487c
Source dataset
uspto-grants-1998_09
Patent number
US05811435

Reaction notes

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