Triethylamine → 3-Nitro-2-vinylpyridine

HRID 629191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629191
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[B-](F)(F)(F)[CH:12]=[CH2:13].[K+].C(N(CC)CC)C>C(O)(C)C.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]>[N+:8]([C:7]1[C:2]([CH:12]=[CH2:13])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 23679353Potassium vinyltrifluoroborate

Produkt 1

HCID 118296173-Nitro-2-vinylpyridineAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2-chloro-3-nitropyridine (0.20 g, 1.261 mmol), potassium trifluoro(vinyl)borate (0.203 g, 1.514 mmol) and PdCl2(dppf) (0.018 g, 0.025 mmol) dissolved in isopropanol (4 mL) and triethylamine (0.211 mL, 1.514 mmol) was gently purged with stream of nitrogen for a few minutes then heated at 100° C. for 4 h. The reaction was cooled and filtered through CELITE® and the solvent was removed under vacuum. The resulting residue was purified via automated flash chromatography (40 gram silica gel, hex/ethyl acetate). Fractions containing the desired product were collected, combined, and evaporated in vacuo to afford tan oil as final product, 3-nitro-2-vinylpyridine (100 mg, 0.666 mmol, 52.8% yield). HPLC RT (Method N)=1.75 minutes.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through CELITE®
  3. customthe solvent was removed under vacuum
  4. customThe resulting residue was purified
  5. additionFractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-45a867ebb3d44c2c931dd8009d701aa4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315494B2

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