Tributylvinyltin → HCID 67170771, compound

HRID 1506452Notes

Reaction equation

HRID 1506452 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:32](=[CH:33][C:34]=1[CH3:35])[C:13]1=[N:14][O:15][C:16]([C:17]3[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:19][N:18]=3)=[C:12]1[CH2:11][CH2:10]2)(=O)=O.[Cl-].[Li+].[CH2:40]([Sn](CCCC)(CCCC)C=C)[CH2:41]CC>O1CCOCC1.[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>[CH3:35][C:34]1[CH:33]=[C:32]2[C:9]([CH2:10][CH2:11][C:12]3[C:13]2=[N:14][O:15][C:16]=3[C:17]2[C:21]([C:22]([F:24])([F:23])[F:25])=[C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:19][N:18]=2)=[CH:8][C:7]=1[CH:40]=[CH2:41]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 86669912HCID 86669912, compound

Product 1

HCID 67170771HCID 67170771, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl trifluoromethanesulfonate (Preparation 64D, 0.120 g, 0.220 mmol) and lithium chloride (0.014 mL, 0.661 mmol) in dioxane (15 mL) was degassed with nitrogen for 15 minutes. Tributyl(vinyl)stannane (0.077 g, 0.242 mmol) was added followed by the addition of tetrakis(triphenylphosphine) palladium(0) (0.025 g, 0.022 mmol) at room temperature. The resulting reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and filtered. The brownish residue was washed with ethyl acetate (3×10 mL), and the combined filtrates were concentrated under reduce pressure. The residue was chromatographed on silica gel eluting with a mixture of 10% ethyl acetate and 90% hexane to yield 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (0.088 g, 0.137 mmol, 62% yield) as a tan viscous liquid. The product had an HPLC ret. time=4.58 min (condition B). LC/MS M+1=423.30.

Workup

  1. customwas degassed with nitrogen for 15 minutes
  2. customThe resulting reaction mixture
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. washThe brownish residue was washed with ethyl acetate (3×10 mL)
  6. concentrationthe combined filtrates were concentrated
  7. customThe residue was chromatographed on silica gel eluting with a mixture of 10% ethyl acetate and 90% hexane

Sources & evidence

ORD record
ord-1d8dbf7e66704314b560d6855058c86f
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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