1H-1,2,4-Triazole, 5-bromo-1-methyl- → 5-(7-[1,3]Dioxan-2-yl-benzofuran-5-yl)-1-methyl-1H[1,2,4]triazole

HRID 1584782Notes

Reaction equation

HRID 1584782 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:7]=[C:8]([CH:15]2[O:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=1)CCC.Br[C:30]1[N:34]([CH3:35])[N:33]=[CH:32][N:31]=1>C1(C)C=CC=CC=1.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>[O:20]1[CH2:19][CH2:18][CH2:17][O:16][CH:15]1[C:8]1[C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=[C:6]([C:30]2[N:34]([CH3:35])[N:33]=[CH:32][N:31]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 1401211H-1,2,4-Triazole, 5-bromo-1-methyl-HCID 21220869HCID 21220869, compound

Product 1

HCID 212208495-(7-[1,3]Dioxan-2-yl-benzofuran-5-yl)-1-methyl-1H[1,2,4]triazoleYield 35.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of tributyl-(7-[1,3]dioxan-2-ylbenzofuran-5-yl)stannane (839 mg), 5-bromo-1-methyl-1H-[1,2,4]triazole (396 mg), bis(triphenylphosphine)palladium (II) chloride (59 mg) in dry toluene (10 ml) was heated at reflux for 42 h. The cooled solution was then filtered through Hyflo and the filtrate washed with 10% potassium fluoride solution (30 ml). The organic layer was washed with brine (30 ml), dried, and evaporated in vacuo to give a yellow oil. The crude material was purified by FCC eluting with hexane:ethyl acetate (1:1→1:3) to give the title compound as a yellow oil (171 mg,).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 42 h
  3. filtrationThe cooled solution was then filtered through Hyflo
  4. washthe filtrate washed with 10% potassium fluoride solution (30 ml)
  5. washThe organic layer was washed with brine (30 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customto give a yellow oil
  9. customThe crude material was purified by FCC
  10. washeluting with hexane:ethyl acetate (1:1→1:3)

Sources & evidence

ORD record
ord-8ae8b9a041e5485690cd599915b31973
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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