Tributylvinyltin → HCID 90416820, compound

HRID 633568Notes

Reaction equation

HRID 633568 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[CH:18]=[C:19]2[C:27]([C:28]3[CH:33]=[C:32]([CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:31]=[CH:30][C:29]=3[O:39][C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=3[F:47])=[CH:26][N:25]([CH3:48])[C:20]2=[C:21]([O:23][CH3:24])[N:22]=1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:47][C:41]1[CH:42]=[C:43]([F:46])[CH:44]=[CH:45][C:40]=1[O:39][C:29]1[CH:30]=[CH:31][C:32]([CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][C:28]=1[C:27]1[C:19]2[C:20](=[C:21]([O:23][CH3:24])[N:22]=[C:17]([CH:1]=[CH2:2])[CH:18]=2)[N:25]([CH3:48])[CH:26]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 90416822HCID 90416822, compound

Product 1

HCID 90416820HCID 90416820, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Tributyl(vinyl)tin (0.053 g, 0.167 mmol), the product from Example 91E (0.075 g, 0.140 mmol) and Pd(PPh3)2Cl2 (9.80 mg, 0.014 mmol) were combined in dioxane (1.163 mL) and sparged with argon for 15 minutes. The mixture was stirred for 2 hours at 100° C., cooled and partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), treated with 3-mercaptopropyl functionalized silica gel, filtered, and concentrated. Purification by chromatography (silica gel, 0-40% ethyl acetate in heptanes) afforded the title compound (0.041 g, 61%).

Workup

  1. customsparged with argon for 15 minutes
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous Na2SO4)
  6. additiontreated with 3-mercaptopropyl functionalized silica gel
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by chromatography (silica gel, 0-40% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-328d943d8ed14f94acc41f650771ba95
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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