Cesium carbonate → N-[5-(2-fluoro-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 2100699

Reaktionsgleichung

Reaktionsgleichung von HRID 2100699
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Pd].O1CCOCC1>[F:24][C:25]1[C:30]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[CH:29][CH:28]=[CH:27][N:26]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27832702-Fluoropyridine-3-boronic acidHCID 46899809N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

Produkt 1

HCID 11709762N-[5-(2-fluoro-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of Intermediate 2 (65 mg, 0.18 mmol) and cesium carbonate (1.5 eq, 88 mg, 0.27 mmol) in a 3:1 mixture of 1,4-dioxan:water (4 ml) was degassed with argon for 5 minutes. Then the mixture was added to (2-fluoro-3-pyridinyl)boronic acid (1.1 eq, 28 mg, 0.20 mmol, Asymchem International Inc.). Palladium acetate (2 mg, 0.01 mmol—alternatively, solid supported palladium may be used), and triphenylphosphine (9 mg, 0.03 mmol) were then added and the whole mixture stirred at reflux for 16 h. The reaction mixture was allowed to cool and partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was separated, dried and evaporated. The resulting product was purified using mass directed preparative HPLC to give the title compound (22 mg, 37%).

Aufarbeitung

  1. customwater (4 ml) was degassed with argon for 5 minutes
  2. additionwere then added
  3. temperatureat reflux for 16 h
  4. temperatureto cool
  5. custompartitioned between ethyl acetate (10 ml) and water (10 ml)
  6. customThe organic layer was separated
  7. customdried
  8. customevaporated
  9. customThe resulting product was purified

Quellen und Nachweise

ORD-Eintrag
ord-6e6c4d9543bf4da5846922de8f093690
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572819B2

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