Tributylvinyltin → 7-Amino-4-vinylisoindolinone

HRID 21186

Reaction equation

HRID 21186 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[CH:13]([Sn](CCCC)(CCCC)CCCC)=[CH2:14]>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]=[CH2:14])=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 197019327-Amino-4-bromo-2,3-dihydroisoindol-1-one

Product 1

HCID 684886597-Amino-4-vinylisoindolinoneYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 1 of Example 10, 7-amino-4-bromoisoindolinone (300 mg, 1.32 mmol) was dissolved in THF (12 mL), and the solution was treated with vinyltributyltin (1.16 mL, 3.96 mmol) and bis(o-toluoylphosphine)dichloropalladium (166 mg, 0.211 mmol), followed by purification by slurry using hexane and chloroform to obtain 7-amino-4-vinylisoindolinone (155 mg, yield 68%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-dd23c3d5e843441b888f71abd7d17ffd
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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