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Potassium Carbonate → 3-Fluoro-5-(5-((2-methylthiazol-4-yl)ethynyl)pyridin-2-yl)benzonitrile

HRID 1913908
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1913908
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)=[CH:4][N:3]=1.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:24]=1)[C:20]#[N:21].C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]3[N:11]=[C:12]([CH3:15])[S:13][CH:14]=3)=[CH:4][N:3]=2)[CH:24]=1)[C:20]#[N:21]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 115649112-Chloro-5-[(2-methyl-4-thiazolyl)ethynyl]pyridineHCID 467381943-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Produkt 1

HCID 166629483-Fluoro-5-(5-((2-methylthiazol-4-yl)ethynyl)pyridin-2-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476
HCID 178418476, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-chloro-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine (30 mmol, 7.02 g) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (30 mmol, crude material, above procedure), dichlorobis(triphenylphosphine)palladium(II) (1.5 mmol, 1.05 g), and potassium carbonate (120 mmol, 16.6 g) were added to deoxygenated DME:water (1:1, 300 mL) at room temperature. The reaction was warmed to 80° C. and stirred overnight under nitrogen, then partitioned in a separatory funnel with EtOAc (500 mL) and water (300 mL). The organic layer was washed with one additional portion of water (100 mL) and the combined aqueous layers back extracted with EtOAc (100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was chromatographed on SiO2, eluting with 30% EtOAc in hexanes, to afford the title compound as a tan solid. 1H-NMR (CDCl3, 500 MHz) δ 8.89 (m, 1H), 8.17 (dd, 1H), 8.04 (m, 1H), 7.98 (dd, 1H), 7.75 (d, 1H), 7.50 (s, 1H), 7.42 (m, 1H), 2.79 (s, 3H). MS (ESI) 320.0 (M+H+).

Aufarbeitung

  1. customto deoxygenated DME:water (1:1, 300 mL) at room temperature
  2. custompartitioned in a separatory funnel with EtOAc (500 mL) and water (300 mL)
  3. washThe organic layer was washed with one additional portion of water (100 mL)
  4. extractionthe combined aqueous layers back extracted with EtOAc (100 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was chromatographed on SiO2
  9. washeluting with 30% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4944e104623b42d594e55d2f5eb065ce
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08609852B2

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