Chlorotrimethylsilane → ethyl (2E)-5-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]-5-hydroxypent-2-enoate

HRID 469249Notes

Reaction equation

HRID 469249 reaction equation
C1COCC1.Cl[Si](C)(C)C.Br[CH2:12]/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH:20]1([NH:26][C:27]2[CH:36]=[C:35]3[C:30]([C:31](=[O:44])[C:32]([CH:42]=[O:43])=[CH:33][N:34]3[CH:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[CH:29][C:28]=2[F:45])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>[Zn].O>[CH:20]1([NH:26][C:27]2[CH:36]=[C:35]3[C:30]([C:31](=[O:44])[C:32]([CH:42]([OH:43])[CH2:12]/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:33][N:34]3[CH:37]([CH2:38][CH3:39])[CH2:40][CH3:41])=[CH:29][C:28]=2[F:45])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 5373944Ethyl (E)-4-bromobut-2-enoateHCID 86633064HCID 86633064, compound

Product 1

HCID 66637082ethyl (2E)-5-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]-5-hydroxypent-2-enoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

2.0 ml of THF and 0.071 ml of chlorotrimethylsilane were added to 73 mg of zinc, followed by stirring at room temperature for 15 minutes. Then, 200 mg of ethyl (2E)-4-bromobut-2-enoate was added thereto, followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde, followed by overnight stirring at room temperature. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 30 mg of ethyl (2E)-5-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]-5-hydroxypent-2-enoate.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. waitfollowed by overnight
  3. stirringstirring at room temperature
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with aqueous saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under a reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a127243c54bb4fe28f95ab25615b70c2
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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