Tributylvinyltin → HCID 22052505, compound

HRID 1369921Notes

Reaction equation

HRID 1369921 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][CH2:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[CH:16]([Sn](CCCC)(CCCC)CCCC)=[CH2:17]>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>[CH:16]([C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:15][CH2:14][CH2:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1)=[CH2:17]

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 15429321HCID 15429321, compound

Product 1

HCID 22052505HCID 22052505, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

A solution of 2.0 g (7.6 mmol) of 7-bromo-1,2,3,5-tetrahydrocyclopenta[c]-quinolin-4-one, 2.6 ml (9.9 mmol) of vinyltributyltin and 0.44 g (0.38 mmol) of tetrakis(triphenylphosphine)palladium is degassed and aerated with nitrogen. After 6 hours of heating to 110° C., the batch is concentrated by evaporation and the residue is taken up on silica gel. Column chromatography on silica gel with hexane-ethyl acetate yields 1.41 g of product.

Workup

  1. concentrationthe batch is concentrated by evaporation

Sources & evidence

ORD record
ord-8d12d6c328b34ea7996cd90b12fa0164
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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