Sodium Cyanide → Methyl 5-cyano-2-(4-fluorophenoxy)nicotinate

HRID 1293201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1293201
Br[C:2]1[CH:3]=[N:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C-:20]#[N:21].[Na+]>C(#N)CC.[Cu](I)I>[C:20]([C:2]1[CH:3]=[N:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:21]

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 57572305HCID 57572305, Verbindung

Produkt 1

HCID 69051385Methyl 5-cyano-2-(4-fluorophenoxy)nicotinateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 7854PropionitrileLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-bromo-2-(4-fluorophenoxy)nicotinate (step 1, 163 mg, 0.50 mmol), sodium cyanide (49 mg, 1.0 mmol), tetrakis(triphenylphohphine) palladium(0) (29 mg, 0.025 mmol), and copper iodide (9.5 mg, 0.05 mmol) in propionitrile (4.0 mL) was heated under reflux for 4.5 h with stirring. The reaction mixture was filtered through a pad of Celite®. The filtrate was partitioned between water (10 mL) and dichloromethane (30 mL). The organic phase was separated, dried (sodium sulfate), and concentrated. The residue was purified by TLC plate developing with hexane/ethyl acetate (3/1) to afford 97 mg (71%) of the title compound: 1H-NMR (CDCl3) δ 8.5 (2H, m), 7.14 (2H, d, J=1.2 Hz), 7.12 (2H, s), 3.99 (3H, s); MS (ESI) m/z 272 (M+).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 h
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. customThe filtrate was partitioned between water (10 mL) and dichloromethane (30 mL)
  5. customThe organic phase was separated
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by TLC plate

Quellen und Nachweise

ORD-Eintrag
ord-78234e9beb5d4c90a635478c61814a85
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238714B2

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