4-Chloro-3-nitropyridine → 4-Cyclohexenyl-3-nitropyridine

HRID 69874

Reaktionsgleichung

Reaktionsgleichung von HRID 69874
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1(B(O)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1>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].C(Cl)Cl.COCCOC>[C:11]1([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1

Komponenten

5

Edukt 2

HCID 27357814-Chloro-3-nitropyridineHCID 38629021-Cyclohexenylboronic acid

Produkt 1

HCID 690448894-Cyclohexenyl-3-nitropyridineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-3-nitro pyridine (1 eq.), cyclohexenyl boronic acid (1.7 eq.), and Pd(dppf)Cl2—CH2Cl2 (0.05 eq) in 3:1 DME/2M Na2CO3, at a concentration of 0.1 M was heated at 95° C. for 16 hours. Upon cooling the reaction was partitioned between EtOAc and H2O, was washed with NaCl(sat.), dried over MgSO4, was filtered and the volatiles were removed in vacuo. The material was purified by SiO2 chromatography (20% EtOAc/hexanes eluant) to yield 4-cyclohexenyl-3-nitropyridine (82%). LCMS (m/z): 205.0 (MH+); LC Rt=3.84 min.

Aufarbeitung

  1. temperatureUpon cooling the reaction
  2. customwas partitioned between EtOAc and H2O
  3. washwas washed with NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. filtrationwas filtered
  6. customthe volatiles were removed in vacuo
  7. customThe material was purified by SiO2 chromatography (20% EtOAc/hexanes eluant)

Quellen und Nachweise

ORD-Eintrag
ord-e9a23e06244e4836baba6265ef0bfc7a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822497B2

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