Trimethyl((tributylstannyl)ethynyl)silane → Ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-trimethylsilylethinyl-4-oxo-3-quinolinecarboxylate

HRID 1901493Notes

Reaction equation

HRID 1901493 reaction equation
Br[C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.C([Sn]([C:37]#[C:38][Si:39]([CH3:42])([CH3:41])[CH3:40])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH:15]1([N:7]2[C:8]3[C:3](=[C:2]([C:37]#[C:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:11]([F:12])=[C:10]([F:13])[C:9]=3[F:14])[C:4](=[O:23])[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6]2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 22924353Ethyl 5-bromo-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 22924385Ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-trimethylsilylethinyl-4-oxo-3-quinolinecarboxylateYield 78.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.95 g of ethyl 5-bromo-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 2.7 g of tributylstannyl-trimethylsilyl-acetylene and 0.29 g of tetrakis-(triphenylphosphine)palladium(0) are refluxed for 4 hours in 20 ml of absolute toluene under a nitrogen atmosphere. The reaction mixture is filtered at room temperature; the solid is washed with a small amount of toluene and dried. 1.6 g of the title compound are obtained (78% of theory).

Workup

  1. filtrationThe reaction mixture is filtered at room temperature
  2. washthe solid is washed with a small amount of toluene
  3. customdried

Sources & evidence

ORD record
ord-c92f61cdd32a4880bbb68a59e2cba3d1
Source dataset
uspto-grants-1996_11
Patent number
US05578604

Reaction notes

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