2-(Tributylstannyl)furan → HCID 15429322, compound

HRID 1937017Notes

Reaction equation

HRID 1937017 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 7-bromo-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one (1.32 g, 5.0 mmol) in toluene (200 ml) is mixed with 2-(tributylstannyl)furan (1.7 ml, 5.5 mmol) and tetrakis(triphenylphosphine)palladium (0.29 g, 0.25 mmol). 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-416d0d4a48a747098644ccc14c15fc8d
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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