Tris(furan-2-yl)phosphane → HCID 2819962, compound

HRID 564224Notes

Reaction equation

HRID 564224 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C([Sn](CCCC)(CCCC)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)CCC>CN(C=O)C>[N:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 6077842-(Tributylstannyl)pyridine

Product 1

HCID 2819962HCID 2819962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To methyl 5-bromo-thiophene-2-carboxylate (2 g), tri-2-furylphosphine (400 mg), and tris(dibenzylidineacetone)dipalladium(0) (400 mg) was added DMF (50 mL), 2-(tributylstannyl)pyridine (4 g) and TEA (1 mL) The mixture was heated at 80° C. for 7 hours, cooled and partitioned between ethyl acetate and brine. The aqueous phase was extracted with ethyl acetate, and the extract was dried, filtered and concentrated. The concentrate was flash chromatographed on silica gel with a 20-70% ethyl acetate in hexane.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and brine
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. customthe extract was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel with a 20-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6bb7061b7e5f463fbdbdbfab265cbcbf
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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