Cesium carbonate → N-[5-(4-methyl-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 2100701

Reaktionsgleichung

Reaktionsgleichung von HRID 2100701
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)O1.Br[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:33][C:32]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH:13]([NH:18][S:19]([CH:22]([CH3:23])[CH3:24])(=[O:20])=[O:21])[CH2:12]2

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 8176303-Bromo-4-methylpyridineHCID 46899971N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

Produkt 1

HCID 11638499N-[5-(4-methyl-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of Intermediate 3 (80 mg, 0.22 mmol), 3-bromo-4-methylpyridine (1 eq, 38 mg, 0.22 mmol) and cesium carbonate (1.5 eq, 108 mg, 0.33 mmol) in a 3:1 mixture of 1,4-dioxan:water (4 ml) was degassed with argon for 5 minutes. Palladium acetate (2 mg, 0.01 mmol), followed by triphenylphosphine (12 mg, 0.04 mmol) were then added and the whole mixture stirred at 160° C. for 20 mins in a microwave reactor. The reaction mixture was allowed to cool and partitioned between ethyl acetate and water. The organic layer was separated and evaporated under reduced pressure. The resulting product was purified on a 5 g Isolute™ Flash silica-gel column, eluting from 0-40% ethyl acetate in petroleum ether to give the title compound as a yellow oil (38 mg, 52%).

Aufarbeitung

  1. customwater (4 ml) was degassed with argon for 5 minutes
  2. additionwere then added
  3. temperatureto cool
  4. custompartitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. customevaporated under reduced pressure
  7. customThe resulting product was purified on a 5 g Isolute™ Flash silica-gel column
  8. washeluting from 0-40% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-41c6bea85eaf422bbf2725e0b379016d
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572819B2

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