Phenyl chloroformate → HCID 18467270, compound

HRID 370232Notes

Reaction equation

HRID 370232 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, relfuxed 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. waitrelfuxed 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-4dca1cd4f0e74541b5bc57a1753e67ec
Source dataset
uspto-grants-2000_10
Patent number
US06140345

Reaction notes

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