2-(Tributylstannyl)pyridine → 3-(5-(2-Pyridyl)-2-furyl)-benzonitrile

HRID 432005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432005
Br[C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Pd+2]>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 6077842-(Tributylstannyl)pyridine2×HCID 219426553-(5-Bromofuran-2-yl)-benzonitrile2×

Produkt 1

HCID 219424103-(5-(2-Pyridyl)-2-furyl)-benzonitrileAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6097231Methanidylbenzene;palladium(2+);triphenylphosphane;chlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Similarly, Pd(PPh3)4 (22 mg, 0.019 mmol) was added to a solution of 3-(5-bromofuran-2-yl)-benzonitrile (35 mg, 0.14 mmol) and 2-tributylstannylpyridine (71 mg, 0.19 mmol) in toluene (2 mL) under argon. In a similar manner, benzylbis(triphenylphosphine)palladium(II) chloride (10.5 mg, 0.014 mmol) was added to a solution of 3-(5-bromofuran-2-yl)-benzonitrile (35 mg, 0.14 mmol) and 2-tributylstannylpyridine (75 mg, 0.20 mmol) in toluene (2 mL) under argon. Both solutions were stirred at 110° C. for 18 h. After cooling to room temperature, the mixtures were combined since TLC of both reactions proved to be identical. The solvent was removed in vacuo from the combined product. Chromatography (5g silica gel SPE tube, dichloromethane) followed by triturating with 10% ethyl acetate in hexanes afforded 26.2 mg (38%) of 3-(5-(2-pyridyl)-2-furyl)-benzonitrile. 1H-NMR (CDCl3), δ (ppm): 8.63 (d, 1H), 8.05 (s, 1H), 7.96 (d, 1H), 7.77 (m, 3H), 7.54 (m, 2H), 7.20 (m, 1H), 6.89 (d, 1H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customThe solvent was removed in vacuo from the combined product
  3. customby triturating with 10% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f4ff63ca18914d17a7609457c8247337
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660753B2

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