Trimethyl((tributylstannyl)ethynyl)silane → HCID 22924388, compound

HRID 2258124Notes

Reaction equation

HRID 2258124 reaction equation
Br[C:2]1[C:11]([F:12])=[C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:9]([F:20])=[C:8]2[C:3]=1[C:4](=[O:29])[C:5]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6][N:7]2[CH:21]1[CH2:23][CH2:22]1.C([Sn](C#[C:44][Si:45](C)([CH3:47])[CH3:46])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:21]1([N:7]2[C:8]3[C:3](=[C:2]([Si:45]([CH3:47])([CH3:46])[CH3:44])[C:11]([F:12])=[C:10]([N:13]4[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]4)[C:9]=3[F:20])[C:4](=[O:29])[C:5]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6]2)[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 22924358HCID 22924358, compound

Product 1

HCID 22924388HCID 22924388, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

1.1 g of ethyl 5-bromo-1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylate, 1.2 g of tributylstannyl-trimethylsilylacetylene and 0.135 g of tetrakis(triphenylphosphine)palladium(0) are refluxed for 3 hours in 10 ml of absolute toluene. The reaction mixture is treated with a further 5 ml of toluene and filtered while hot. The product crystallizes out of the filtrate. After filtration with suction and drying, 0.63 g of the title compound is obtained (56% of theory).

Workup

  1. filtrationfiltered while hot
  2. customThe product crystallizes out of the filtrate
  3. filtrationAfter filtration with suction
  4. customdrying

Sources & evidence

ORD record
ord-5e5dd8864dd54453851c9c471c35546c
Source dataset
uspto-grants-1997_08
Patent number
US05659038

Reaction notes

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