(Diethylamino)sulfur trifluoride → Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1584818Notes

Reaction equation

HRID 1584818 reaction equation
[Br:1][C:2]1[C:11]([CH2:12]O)=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23].C(N(S(F)(F)[F:30])CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:11]([CH2:12][F:30])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 21220404Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 21220400Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

In 127 ml of methylene chloride was suspended 1.27 g of ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, and 1.33 g of diethylaminosulfur trifluoride was dropwise added to the suspension at -40° C., after which the resulting mixture was stirred at -20° C. for one hour and then at 0° C. for three hours. The reaction mixture was added to 120 ml of ice water and the pH was adjusted to 8 with a saturated aqueous sodium hydrogencarbonate solution. Thereafter, the organic layer formed was separated, washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluent: chloroform:ethanol=100:1), to obtain 1.05 g of colorless, crystalline ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. additionwas dropwise added to the suspension at -40° C.
  2. waitat 0° C. for three hours
  3. customThereafter, the organic layer formed
  4. customwas separated
  5. washwashed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography (eluent: chloroform:ethanol=100:1)

Sources & evidence

ORD record
ord-5718d3e101064c7595b275e68965cc43
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

Loading…