Sodium hydride → Ethyl 1-(2-fluorocyclopropyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 2351025Notes

Reaction equation

HRID 2351025 reaction equation
C(OC=C(C(=O)C1C=C(F)C(F)=CC=1F)C(OCC)=O)C.NC1CC1F.FC(F)(F)C([O-])=O.[F:34][C@H:35]1[CH2:37][C@H:36]1[NH:38][CH:39]=[C:40]([C:46](=[O:56])[C:47]1[CH:52]=[C:51]([F:53])[C:50]([F:54])=[CH:49][C:48]=1F)[C:41]([O:43][CH2:44][CH3:45])=[O:42].[H-].[Na+]>O1CCOCC1.C(N(CC)CC)C>[F:34][CH:35]1[CH2:37][CH:36]1[N:38]1[C:48]2[C:47](=[CH:52][C:51]([F:53])=[C:50]([F:54])[CH:49]=2)[C:46](=[O:56])[C:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:39]1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 84468TrifluoroacetateHCID 101976142-Fluoro-cyclopropanamineHCID 54008204Ethyl 3-(2,4,5-trifluorophenyl)-3-oxo-2-(ethoxymethylene)propanoateHCID 178472046HCID 178472046, compound

Product 1

HCID 21999370Ethyl 1-(2-fluorocyclopropyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

As for the method for producing the starting materials, an example for the preparation of the compound (IIa) is described below: ##STR7## That is, ethyl 3-ethoxy-2-(2,4,5-trifluorobenzoyl)acrylate (VIa; R4 =C2H5) is reacted with 1-amino-2-fluorocyclopropane (or an acid addition salt thereof such as trifluoroacetate in the presence of at least a molar equivalent of a proper base such as triethylamine), and the resulting ethyl 3-(cis-2-fluorocyclopropyl)amino-2-(2,4,5-trifluorobenzoyl)acrylate (VIIa; R4 =C2H5) can be reacted with approximately a molar equivalent of sodium hydride in a solvent such as anhydrous dioxane at a temperature of from 20° C. to 50° C. to yield ethyl 1-(2-fluorocyclopropyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (IIa; R4 =C2H5) in good yield.

Workup

  1. customAs for the method for producing the starting materials
  2. additionan acid addition salt

Sources & evidence

ORD record
ord-d651faecf4da4578beb1ac180e549288
Source dataset
uspto-grants-1989_10
Patent number
US04871852

Reaction notes

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