Allyltributylstannane → HCID 21250472, compound

HRID 1531748Notes

Reaction equation

HRID 1531748 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:21])=[CH:7][C:8]([O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:24]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:21])=[CH:7][C:8]([O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[N:9]2)=[CH:4][CH:3]=1)[CH:23]=[CH2:22]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 21250217HCID 21250217, compound

Product 1

HCID 21250472HCID 21250472, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

6.8 g (0.02 mol) of 4-[(7-bromo-4-methyl-quinolin-2-yl)-oxy]-benzonitrile, 6.8 g (5.9 mmol) of tetrakis-(triphenylphosphine)-palladium (0) and 6.8 ml (0.022 mol) of allyltributyltin are refluxed in 50 ml toluene under a nitrogen atmosphere for 2 hours. The toluene is distilled off, the residue triturated with ether and suction filtered. The mother liquor is combined with silica gel and evaporated down. Then the mixture is chromatographed on silica gel and eluted with cyclohexane/ethyl acetate (95:5 and 9:1). The desired fractions are combined and evaporated down.

Workup

  1. distillationThe toluene is distilled off
  2. customthe residue triturated with ether and suction
  3. filtrationfiltered
  4. customevaporated down
  5. customThen the mixture is chromatographed on silica gel
  6. washeluted with cyclohexane/ethyl acetate (95:5 and 9:1)
  7. customevaporated down

Sources & evidence

ORD record
ord-2133a8546eaa4a2db4dccff2706a54f8
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

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