Tributylvinyltin → HCID 68182011, compound

HRID 1506394Notes

Reaction equation

HRID 1506394 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[C:16]1[O:15][C:14]([C:20]3[O:24][N:23]=[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:21]=3[C:31]([F:34])([F:33])[F:32])=[N:13][C:12]=1[CH2:11][CH2:10]2)(=O)=O.[CH2:37]([Sn](CCCC)(CCCC)C=C)[CH2:38]CC.[Cl-].[Li+]>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>[C:25]1([C:22]2[C:21]([C:31]([F:33])([F:32])[F:34])=[C:20]([C:14]3[O:15][C:16]4[C:17]5[C:9](=[CH:8][C:7]([CH:37]=[CH2:38])=[CH:19][CH:18]=5)[CH2:10][CH2:11][C:12]=4[N:13]=3)[O:24][N:23]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 86669892HCID 86669892, compound

Product 1

HCID 68182011HCID 68182011, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]oxazol-7-yl trifluoromethanesulfonate (Preparation 48A, 140 mg, 0.264 mmol) in dioxane (1 mL) in a 150 mL sealed tube were sequentially added tributyl(vinyl)tin (0.085 mL, 0.290 mmol), lithium chloride (33.6 mg, 0.792 mmol), and tetrakis(triphenylphosphine)palladium(0) (30.5 mg, 0.026 mmol). The solution was purged with argon for 5 mins. It was stirred for 20 hrs in a 100° C. oil bath. After cooling, the solution was diluted with ˜20 mL of ether and filtered thru CELITE® and evaporated to give an oily residue. The residue was purified by Combiflash (24 g silica gel) eluting with 1:9 followed by 2:8 EtOAc-hexane to give 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[2,1-d]oxazole (49.4 mg, 46% yield). LC/MS M+1=409.25.

Workup

  1. customThe solution was purged with argon for 5 mins
  2. temperatureAfter cooling
  3. additionthe solution was diluted with ˜20 mL of ether
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oily residue
  7. customThe residue was purified by Combiflash (24 g silica gel)
  8. washeluting with 1:9

Sources & evidence

ORD record
ord-868755f816ee4b0393f88215d1b3f5e4
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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