Diiodomethane → 4-Cyclopropyl-3-iodopyridine

HRID 523578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523578
N(OCCC(C)C)=O.[CH:9]1([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2N)[CH2:11][CH2:10]1.[I:19]CI>C1COCC1.[Cu](I)I>[CH:9]1([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[I:19])[CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 668019694-Cyclopropylpyridin-3-amine

Produkt 1

HCID 668018874-Cyclopropyl-3-iodopyridineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Isoamyl nitrite (2.62 gm, 22.38 mmol) was added to the stirred solution of 4-cyclopropylpyridin-3-amine (1.0 g, 7.46 mmol) in dry THF (15 mL) under argon atmosphere. This was followed by the addition of diiodomethane (3.0 mL, 22.38 mmol) and copper iodide (1.42 g, 7.46 mmol). The resulting mixture was refluxed at 80° C. for 1 hour. The reaction mixture was cooled, filtered and the filtrate was partitioned between ethyl acetate and water. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 600 mg of the product (34% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was partitioned between ethyl acetate and water
  4. concentrationThe organic layer was concentrated
  5. customto yield the crude product
  6. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e8ee5bf82e0f42acbe5dd72078814123
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339501B2

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