Tributylvinyltin → HCID 68801993, compound

HRID 2250599Notes

Reaction equation

HRID 2250599 reaction equation
[Cl-].[Li+].Cl[C:4]1[CH:9]=[C:8]([C:10]2[C:11]3[N:12]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:13]=[C:14]([CH3:25])[C:15]=2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:7]=[CH:6][N:5]=1.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC.[F-].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:29]([C:26]1[N:12]2[N:13]=[C:14]([CH3:25])[C:15]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([CH:31]=[CH2:32])[CH:9]=3)[C:11]2=[CH:28][CH:27]=1)[CH3:30]

Participants

9

Reactant 4

HCID 81998Tributylvinyltin2×HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 86597472HCID 86597472, compound

Product 1

HCID 68801993HCID 68801993, compoundYield 28.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 178418397HCID 178418397, compoundSolvent

Procedure

To lithium chloride (16.5 mg) was added a solution of ethyl 5-[4-(2-chloro-4-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (65 mg) and tributyl(vinyl)stannane (56.7 mg) in dioxane (1 mL) and tetrakis(triphenylphosphine)palladium(0) (1.9 mg). The mixture was refluxed. After 4 hours, tributyl(vinyl)stannane (50 mg) and tetrakis(triphenylphosphine)palladium(0) (1.9 mg) was added. After refluxed over night, the reaction mixture was quenched with potassium fluoride (1.8 mmol) in H2O. The mixture was filtered through Celite and was washed with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash silica gel chromatography (silica gel, 50 mL) eluted with hexane-ethyl acetate=5-1 and 3-1 to give ethyl 5-[7-ethyl-2-methyl-4-(2-vinyl-4-pyridinyl)pyrrolo[1,2-b]pyridazin-3-yl]pentanoate (18 mg, 28.3%) as an yellow oil.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureAfter refluxed over night
  3. filtrationThe mixture was filtered through Celite
  4. washwas washed with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by flash silica gel chromatography (silica gel, 50 mL)
  10. washeluted with hexane-ethyl acetate=5-1 and 3-1

Sources & evidence

ORD record
ord-43a3535045a6498ab893829d019a5c62
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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