Tributylvinyltin → HCID 89590961, compound

HRID 522417Notes

Reaction equation

HRID 522417 reaction equation
[C:1]([C@H:5]1[C:39](=[O:40])[N:38]2[CH2:41][C@@H:35]([CH2:36][C@H:37]2[C:42]([O:44][CH3:45])=[O:43])[O:34][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25](OS(C(F)(F)F)(=O)=O)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:46][C@H:9]2[O:8][C:7](=[O:47])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:48]([Sn](CCCC)(CCCC)C=C)[CH2:49]CC>O1CCOCC1.[Cu]I.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:1]([C@H:5]1[C:39](=[O:40])[N:38]2[CH2:41][C@@H:35]([CH2:36][C@H:37]2[C:42]([O:44][CH3:45])=[O:43])[O:34][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([CH:48]=[CH2:49])=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:46][C@H:9]2[O:8][C:7](=[O:47])[NH:6]1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 89590960HCID 89590960, compound

Product 1

HCID 89590961HCID 89590961, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from Example 244 step 1 (100 mg, 0.146 mmol) in dioxane (3 ml) was added tributyl(vinyl)stannane (92 mg, 0.292 mmol), copper (I) iodide (5.55 mg, 0.029 mmol) and tetrakis (33.7 mg, 0.029 mmol). After purging with N2 for 5 min, the reaction was stirred at 80° C. for 16 hours. After cooling to room temperature, water was added and the reaction was extracted with ethyl acetate, washed with brine, dried (Na2SO4) and concentrated. Purification by PTLC (30% EtOAc/hexane) provided the desired compound.

Workup

  1. customAfter purging with N2 for 5 min
  2. temperatureAfter cooling to room temperature
  3. additionwater was added
  4. extractionthe reaction was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by PTLC (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-86fcb7fc8b5b4c6794f8639c4f8ab67d
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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