Potassium Phosphate, Tribasic → 2-(5-Fluoro-pyridin-3-yl)-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one

HRID 1843869

Reaktionsgleichung

Reaktionsgleichung von HRID 1843869
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([F:23])[CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:23][C:21]1[CH:22]=[C:17]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=3)[C:10]2=[O:13])[CH:18]=[N:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 8202063-Bromo-5-fluoropyridineHCID 668015937-(Trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one

Produkt 1

HCID 668073242-(5-Fluoro-pyridin-3-yl)-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-oneAusbeute 27,19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using analogous reaction conditions as described in Example 1, 7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-16c: 90 mg, 0.419 mmol) was reacted with 3-bromo-5-fluoro-pyridine (73.67 mg, 0.419 mmol), 1,4-dioxane (10 mL), copper iodide (7.98 mg, 0.0419 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (17.85 mg, 0.126 mmol) and potassium phosphate (222 mg, 1.048 mmol) to afford the crude product. Purification by column chromatography on silica gel (0.5% methanol in DCM) afforded 35 mg of the product (27.19% yield).

Aufarbeitung

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (0.5% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-1d82c553e1ec4bf286dd41da411a7f39
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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