Potassium Phosphate, Tribasic → HCID 89964195, Verbindung

HRID 1843980

Reaktionsgleichung

Reaktionsgleichung von HRID 1843980
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[C:35]1(=[O:48])[C:40]2[C:41]3[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=3[S:43][C:39]=2[CH2:38][CH2:37][NH:36]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:58]1[CH:59]=[N:60][CH:61]=[CH:62][C:63]=1[C:64]([F:67])([F:66])[F:65]>CCCCCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O1CCOCC1>[F:65][C:64]([F:67])([F:66])[C:63]1[CH:62]=[CH:61][N:60]=[CH:59][C:58]=1[N:36]1[CH2:37][CH2:38][C:39]2[S:43][C:42]3[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=3[C:40]=2[C:35]1=[O:48]

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 200749053,4-Dihydro-[1]benzothieno[3,2-c]pyridin-1(2H)-one

Produkt 1

HCID 89964195HCID 89964195, VerbindungAusbeute 8,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

X-Phos (35 mg, 0.0739 mmol) and Pd2(dba)3 (45 mg, 0.0492 mmol) were added to a previously degassed solution of 3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one (I-9d: 100 mg, 0.4919 mmol), K3PO4 (313 mg, 1.4759 mmol) and 1,4-dioxane (5 mL) in a sealed tube. This was followed by the addition of 3-bromo-4-(trifluoromethyl)pyridine (134 mg, 0.5903 mmol) and the resulting reaction mass was heated at 120° C. for 48 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was partitioned between water and ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (30% ethyl acetate in hexane), followed by preparative HPLC afforded 14 mg of the product (8.18% yield).

Aufarbeitung

  1. customthe resulting reaction mass
  2. customThe reaction mass was partitioned between water and ethylacetate
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8cd24f5d3ff54ae98a9702cdbd79f083
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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