Tributylvinyltin → HCID 22718567, compound

HRID 1582609Notes

Reaction equation

HRID 1582609 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15](Br)=[C:16]([CH2:17][CH2:18][CH2:19][NH2:20])[C:11]=2[O:10][CH:9]1[CH2:22][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]([Sn](CCCC)(CCCC)CCCC)=[CH2:25]>C1(C)C=CC=CC=1.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]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH:24]=[CH2:25])=[C:16]([CH2:17][CH2:18][CH2:19][NH2:20])[C:11]=2[O:10][CH:9]1[CH2:22][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 22718666HCID 22718666, compound

Product 1

HCID 22718567HCID 22718567, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of N-t-butoxycarbonyl 7-(3-aminopropyl)-6-bromo-2-ethylbenzoxazole (396 mg, 1.03 mmol), vinyltributyltin (360 mg, 1.14 mmol), and tetrakis(triphenylphosphine)palladium (0) (60 mg, 0.052 mmol) in toluene (10 mL) was refluxed for 3 hours. The crude reaction mixture was poured directly on a silica gel column, and the tin by-products were eluted with hexanes. The product was eluted with 25% EtOAc/hexanes to give a clear oil (180 mg, 53%).

Workup

  1. customThe crude reaction mixture
  2. additionwas poured directly on a silica gel column
  3. washthe tin by-products were eluted with hexanes
  4. washThe product was eluted with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-6d14f90d260943a0bac44219bbe3052a
Source dataset
uspto-grants-2004_05
Patent number
US06737431B2

Reaction notes

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