2-Fluoroethyl bromide → HCID 13772828, compound

HRID 868099Notes

Reaction equation

HRID 868099 reaction equation
[H-].[Na+].[C:3]([C:6]1[C:15]([F:16])=[C:14]2[C:9]([C:10](=[O:22])[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][NH:13]2)=[CH:8][C:7]=1[F:23])(=[O:5])[CH3:4].Br[CH2:25][CH2:26][F:27]>CN(C)C=O>[C:3]([C:6]1[C:15]([F:16])=[C:14]2[C:9]([C:10](=[O:22])[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][N:13]2[CH2:25][CH2:26][F:27])=[CH:8][C:7]=1[F:23])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 13772821HCID 13772821, compound

Product 1

HCID 13772828HCID 13772828, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 1.62 g (34.0 mmol) of sodium hydride (50% dispersion in oil, pentane washed) in 250 ml of dimethylformamide was added 10.0 g (34 mmol) of the ethyl 7-acetyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate dissolved in 100 ml of dimethylformamide at room temperature. The mixture was stirred for two hours, and 13.0 g (2.4 eq) of 1-bromo-2-fluoroethane was added. The mixture was stirred overnight at 50° C. It was concentrated, and partitioned between water and dichloromethane. The dichloromethane was then concentrated and the residue purified by column chromatography to give 3.75 g of ethyl 7-acetyl-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3quinoline carboxylate, mp 155°-156° C. This material was hydrolyzed with 2N hydrochloric acid and 2-propanol as co-solvent to give 2.95 g of the 7-acetyl-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, mp 215°-216° C.

Workup

  1. stirringThe mixture was stirred overnight at 50° C
  2. concentrationIt was concentrated
  3. custompartitioned between water and dichloromethane
  4. concentrationThe dichloromethane was then concentrated
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-152f266ce97840d982b5cc5b5df40327
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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