Sodium Iodide → HCID 58182714, Verbindung

HRID 2199615

Reaktionsgleichung

Reaktionsgleichung von HRID 2199615
[NH2:1][C:2]1[C:9](Br)=[CH:8][C:5](C#N)=[CH:4][N:3]=1.[I-:11].[Na+].CN[C@@H]1CCCC[C@H]1[NH:21][CH3:22]>O1CCOCC1.[Cu]I>[I:11][C:9]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([N+:21]#[C-:22])[CH:8]=1

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 14912506-Amino-5-bromopyridine-3-carbonitrileHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Produkt 1

HCID 58182714HCID 58182714, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The mixture of 6-amino-5-bromonicotinonitrile (3.315 g, 15.9 mmol, 1 eq), sodium iodide (4.77 g, 2 eq), copper(I) iodide (303 mg, 0.1 eq), and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.52 mL, 0.2 eq) in anhydrous dioxane (40 mL under nitrogen atmosphere was stirred at 120° C. for 20 hours. The mixture was cooled to room temperature then partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, further washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the crude solid residue was subject to a column chromatography started first with EtOAc-Hex (1:5 to 1:1) followed by MeOH—CHCl3 (1:100 to 1:20). Product containing fractions were all collected and concentrated. The solid residue was triturated with EtOAc-Hex (1:4) yielding 3-iodo-5-isocyanopyridin-2-amine as an off-white solid in the amount of 2.75 g upon filtration.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthen partitioned between ethyl acetate and aqueous ammonium chloride
  3. customThe organic layer was isolated
  4. washfurther washed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe upper solution was decanted
  7. concentrationconcentrated
  8. additionProduct containing fractions
  9. customall collected
  10. concentrationconcentrated
  11. customThe solid residue was triturated with EtOAc-Hex (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-7e1ee5ac571f4c2ca06910a31bacfc15
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359336B2

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