Isoamyl Nitrite → 3-Iodo-2-methyl-6-(trifluoromethyl)pyridine

HRID 604608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604608
N[C:2]1[C:3]([CH3:12])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.N(OCCC(C)C)=O.[I-:21]>C(Cl)(Cl)Cl>[I:21][C:2]1[C:3]([CH3:12])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8053Isoamyl NitriteHCID 30165Iodide IonHCID 35218502-methyl-6-(trifluoromethyl)pyridin-3-amine

Produkt 1

HCID 670577443-Iodo-2-methyl-6-(trifluoromethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-amino-2-methyl-6-(trifluoromethyl)pyridine (500 mg, 2.84 mmol), isoamyl nitrite 760 μL, 5.68 mmol) and iodide. (793 mg, 3.12 mmol) in dry CHCl3 (10 mL) was stirred at room temperature for 0.5 h. The mixture was heated at 80° C. under N2 for 4 h. The reaction mixture was quenched with saturated Na2S2O3 then partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 3-iodo-2-methyl-6-(trifluoromethyl)pyridine. LCMS calc.=288.0; found=288.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J=8.0 Hz, 1H); 7.22 (d, J=8.1 Hz, 1H); 2.83 (s, 3H).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated Na2S2O3
  2. customthen partitioned between CH2Cl2 and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Si, 1% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-21869445d738483aa3519101db350f49
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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