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Ammonium Chloride → 2'-Fluoro-5'-[7-(1-hydroxy-1-methylethyl)-[1,8]naphthyridin-4-yl]biphenyl-2-carbonitrile

HRID 1061844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1061844
[C:1]([C:4]1[N:13]=[C:12]2[C:7]([C:8]([C:14]3[CH:15]=[CH:16][C:17]([F:28])=[C:18]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:19]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:29][Mg]Br.[NH4+].[Cl-]>C1COCC1>[F:28][C:17]1[CH:16]=[CH:15][C:14]([C:8]2[C:7]3[C:12](=[N:13][C:4]([C:1]([OH:3])([CH3:29])[CH3:2])=[CH:5][CH:6]=3)[N:11]=[CH:10][CH:9]=2)=[CH:19][C:18]=1[C:20]1[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 99254355'-[7-Acetyl-[1,8]naphthyridin-4-yl]-2'-fluorobiphenyl-2-carbonitrileHCID 178418573HCID 178418573, Verbindung2×

Produkt 1

HCID 101104952'-Fluoro-5'-[7-(1-hydroxy-1-methylethyl)-[1,8]naphthyridin-4-yl]biphenyl-2-carbonitrileAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of 5′-[7-acetyl-[1,8]naphthyridin-4-yl]-2′-fluorobiphenyl-2-carbonitrile (from Example 58) (28.6 mg, 0.0778 mmol) in anhydrous THF (2 mL), cooled under nitrogen to −78° C., was added dropwise methylmagnesium bromide (3.0 M solution in Et2O, 26.0 μL, 0.078 mmol). The mixture was stirred at −78° C. for a total of 85 min, adding more methylmagnesium bromide (3.0 M solution in Et2O, 26.0 μL, 0.078 mmol) after 45 min and 70 min. Saturated aqueous NH4Cl (2 mL) was then added and the mixture was allowed to warm to room temperature. The mixture was partitioned between ethyl acetate (15 mL) and water (10 mL). The aqueous layer was extracted further with ethyl acetate (15 mL), and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 3% MeOH/CH2Cl2, to afford 20.6 mg (69%) of the title compound as a white solid. δH (360 MHz, CDCl3) 1.67 (6H, s), 5.32 (1H, s), 7.44 (1H, t, J 9.1), 7.51 (1H, d, J 4.6), 7.54 (1H, td, J 7.7, 1.1), 7.58-7.65 (4H, m), 7.71 (1H, td, J 7.7, 1.1), 7.84 (1H, dd, J 7.7, 1.1), 8.51 (1H, d, J 8.8), 9.15 (1H, d, J 4.2). m/z (ES+) 384 [MH]+.

Aufarbeitung

  1. custom70 min
  2. temperatureto warm to room temperature
  3. customThe mixture was partitioned between ethyl acetate (15 mL) and water (10 mL)
  4. extractionThe aqueous layer was extracted further with ethyl acetate (15 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with 3% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-2cf696a145784d4e82ad34fd780a1f8b
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06960598B2

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