Water → (1-Methyl-1H-benzoimidazol-2-YL)-[3-(3-phenyl-pyrazin-2-YL)-azetidin-1-YL]-methanone

HRID 1850318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850318
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]([C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)=[O:13])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.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]>[CH3:19][N:18]1[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]=[C:14]1[C:12]([N:10]1[CH2:11][CH:8]([C:3]2[C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1)=[O:13]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58546825HCID 58546825, Verbindung

Produkt 1

HCID 58546740(1-Methyl-1H-benzoimidazol-2-YL)-[3-(3-phenyl-pyrazin-2-YL)-azetidin-1-YL]-methanoneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of [3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-(1-methyl-1H-benzoimidazol-2-yl)-methanone (100 mg, 0.30 mmol) in dioxane (10 mL) was added phenylboronic acid (87 mg, 0.71 mmol), Na2CO3 (152 mg, 1.4 mmol) and H2O (2 mL). The reaction mixture was degassed with N2 and then PdCl2(dppf) (35 mg, 0.05 mmol) was added. The reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was left to reach RT and filtered through a pad of CELITE® and the filter cake was washed with CH2Cl2 (20 mL×3). The combined filtrates were evaporated in vacuo and the residue was purified by column chromatography to give the desired compound (60 mg, 0.17 mmol, yield 70%)

Aufarbeitung

  1. customThe reaction mixture was degassed with N2
  2. waitThe reaction mixture was left
  3. customto reach RT
  4. filtrationfiltered through a pad of CELITE®
  5. washthe filter cake was washed with CH2Cl2 (20 mL×3)
  6. customThe combined filtrates were evaporated in vacuo
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d88ad0087c894acb9ea3ccff4c228d80
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957073B2

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