Lithium Chloride → HCID 10636850, compound

HRID 1957122Notes

Reaction equation

HRID 1957122 reaction equation
[Cl:1][C:2]1[C:3](I)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.[CH2:18](C([SnH3])=C(CCCC)CCCC)[CH2:19]CC.[Cl-].[Li+]>CN(C)C=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[C:3]([CH:18]=[CH2:19])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 10691461HCID 10691461, compoundHCID 21115800Tri(butyl)vinylstannane

Product 1

HCID 10636850HCID 10636850, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6,7-dichloro-2,3-dimethoxy-5-iodoquinoxaline (3.0 g, 7.8 mmol), tributylvinylstannane (4.94 g, 15.6 mmol), lithium chloride (991 mg, 23.4 mmol) and bis(triphenylphosphine)palladium (II) chloride (600 mg, 1.56 mmol) in dry dimethylformamide (100 mL) was heated at 100° C. for 1.5 hours. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with toluene) to give 6,7-dichloro-2,3-dimethoxy-5-ethenylquinoxaline (1.76 g, 79%), as a white solid.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (eluting with toluene)

Sources & evidence

ORD record
ord-e92cd89a7f1c4ed68e5215a64955babb
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

Loading…