Trimethyl((tributylstannyl)ethynyl)silane → HCID 23284663, compound

HRID 369330Notes

Reaction equation

HRID 369330 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([F:35])=[CH:11][C:12]([F:34])=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22]([F:26])[C:23]=3Br)[C:18](=[O:28])[C:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16]2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn]([C:49]#[C:50][Si:51]([CH3:54])([CH3:53])[CH3:52])(CCCC)CCCC)CCC>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.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([F:35])=[CH:11][C:12]([F:34])=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22]([F:26])[C:23]=3[C:49]#[C:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[C:18](=[O:28])[C:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16]2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 10973728HCID 10973728, compound

Product 1

HCID 23284663HCID 23284663, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Ethyl 1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (6 g), tributylstannyltrimethylsilylacetylene (6 g) and tetrakis(triphenylphosphine)palladium (0.4 g) were added to dry toluene (30 ml). This suspension was heated under reflux overnight in a nitrogen atmosphere. After the temperature of the reaction mixture was given back to room temperature, the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with water. After an organic layer was collected and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resultant residue was subjected to column chromatography on silica gel (silica 240 cc/chloroform) to obtain the title compound (4.6 g) as a colorless powder.

Workup

  1. temperatureThis suspension was heated
  2. temperatureunder reflux overnight in a nitrogen atmosphere
  3. customwas given back to room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionEthyl acetate was added to the residue
  6. washthe mixture was washed with water
  7. customAfter an organic layer was collected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c8b7c87be33d4c16a45517cd5a2787b8
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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