1,4-Dioxane → HCID 178522856, compound

HRID 2290021Notes

Reaction equation

HRID 2290021 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16](I)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)CCC.O1CCOCC1.CN1C(=O)N(C)CCC1>O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 178522879HCID 178522879, compound

Product 1

HCID 178522856HCID 178522856, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A deoxygenated mixture of 0.75 g of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 40, 0.75 g of 2-(tributylstannyl)thiophene, 60 mg of bis(triphenylphosphine)palladium(II)dichloride, 7.5 mL of dioxane and 2.5 mL of DMPU is stirred for 2 h at 100° C. The cooled mixture is diluted with 20 mL of hexanes and 60 mL of distilled water. The mixture is stirred for 5 minutes and then filtered. The solid is washed with two 50 mL portions of distilled water and then with two 25 mL portions of methyl t-butyl ether. It is then dissolved in 20 mL of refluxing acetic acid, treated with 2 g of activated carbon and filtered through celite. The volume of the filtrate is reduced to 10 mL and the hot solution diluted with 10 mL of distilled water. Upon cooling, 0.3 g of the title compound precipitates and is collected by filtration.

Workup

  1. filtrationfiltered
  2. washThe solid is washed with two 50 mL portions of distilled water
  3. dissolutionIt is then dissolved in 20 mL of refluxing acetic acid
  4. additiontreated with 2 g of activated carbon
  5. filtrationfiltered through celite
  6. additionthe hot solution diluted with 10 mL of distilled water
  7. temperatureUpon cooling
  8. custom0.3 g of the title compound precipitates
  9. filtrationis collected by filtration

Sources & evidence

ORD record
ord-cd8f27d5a19344278127eb94c1c59771
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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