2-(Tributylstannyl)furan → HCID 15429322, compound

HRID 1831732Notes

Reaction equation

HRID 1831732 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.C([Sn](CCCC)(CCCC)[C:21]1[O:22][CH:23]=[CH:24][CH:25]=1)CCC>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>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[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

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 15429321HCID 15429321, compound

Product 1

HCID 15429322HCID 15429322, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 1.32 g (5.0 mmol) of 7-bromo-1,2,3,5-tetrahydrocyclo-penta[c]quinolin-4-one in 200 mL of toluene is mixed with 1.7 ml (5.5 mmol) of 2-(tributyl-stannyl)furan and 0.29 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium. The reaction mixture is degassed, aerated with nitrogen, stirred for 15 hours at room temperature and heated for 4.5 hours to 110° C. The batch is mixed with silica gel and concentrated by evaporation in a vacuum. Column chromatography of the residue on silica gel with hexane-ethyl acetate yields 1.33 g of product.

Workup

  1. customThe reaction mixture is degassed
  2. temperatureheated for 4.5 hours to 110° C
  3. additionThe batch is mixed with silica gel
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-0edcfa47a2bc45af8150c536366d52de
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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