4-tributylstannyl-5H-furan-2-one → HCID 22346469, compound

HRID 897379Notes

Reaction equation

HRID 897379 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12](I)[N:11]=2)=[O:9])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH2:33][O:32][C:31](=[O:34])[CH:30]=1)CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([C:29]3[CH2:33][O:32][C:31](=[O:34])[CH:30]=3)[N:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 109157024-tributylstannyl-5H-furan-2-oneHCID 22346452HCID 22346452, compound

Product 1

HCID 22346469HCID 22346469, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

The iodide from step 2 (4.37 g, 10.32 mmol) was dissolved in anhydrous toluene (40 ml) in an oven dried flask that was purged with nitrogen. Dichlorobis(triphenylphospine)palladium (II) (660 mgs., 0.94 mmol) and 4-(tributylstannyl)furan-2(5H)-one, (3.85 g, 10.32 mmol) (prepared as described by Gregory J. Hollingworth, Gemma Perkins, and Joseph Sweeney, J. Chem. Soc., Perkins 1. 1996, 1913) were then added to the reaction. After four hours at reflux the reaction was cooled and the solids that precipitated from the solution were collected by vacuum filtration. The product contained 17% of an impurity: N,N′-bis(4-fluorobenzyl)-8,8′-dihydroxy-5,5′-bi-1,6-naphthyridine-7,7′-dicarboxamide.

Workup

  1. customdried flask that
  2. customwas purged with nitrogen
  3. temperatureAfter four hours at reflux the reaction
  4. temperaturewas cooled
  5. customthe solids that precipitated from the solution
  6. filtrationwere collected by vacuum filtration

Sources & evidence

ORD record
ord-4fc55660dccf4039862341bf69191dfa
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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