Potassium Phosphate, Tribasic → HCID 54671271, Verbindung

HRID 1842525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842525
Cl[C:2]1[C:3]([N:8]2[CH2:11][CH:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:23]1([CH3:22])[CH:24]=[CH:25][CH:26]=[C:27]([C:2]2[C:3]([N:8]3[CH2:11][CH:10]([C:12]4[CH:21]=[CH:20][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:13]=4)[CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH:28]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27339503-Tolylboronic acidHCID 58548445HCID 58548445, Verbindung

Produkt 1

HCID 54671271HCID 54671271, VerbindungAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2-[1-(3-chloro-pyrazin-2-yl)-azetidin-3-yl]-quinoline, as prepared in the above Step 3 of Example 57, (150 mg, 0.51 mmol), 3-methyl-phenylboronic acid (75 mg, 0.51 mmol) and K3PO4 (211 mg, 1 mmol) in 1,4-dioxane (12 mL) and H2O (3 mL) was added Pd(dppf)Cl2 (35 mg, 0.05 mmol) then the reaction mixture was stirred at 110° C. under N2 overnight. The reaction mixture was filtered through CELITE™ and washed with CH2Cl2 (50 mL). The organic layer was concentrated and the crude product was purified by silica gel column to give 2-[1-(3-m-tolyl-pyrazin-2-yl)-azetidin-3-yl]-quinoline (50 mg, 0.14 mmol, yield 28%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through CELITE™
  2. washwashed with CH2Cl2 (50 mL)
  3. concentrationThe organic layer was concentrated
  4. customthe crude product was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-d16964469f8f4c1e80969b623864137f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946230B2

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