Sodium Iodide → HCID 125501637, compound

HRID 2199627Notes

Reaction equation

HRID 2199627 reaction equation
BrC1C=C(C#N)C=NC=1.[I-:10].[Na+].[CH3:12][NH:13][C@@H:14]1[CH2:19][CH2:18]CC[C@H:15]1[NH:20][CH3:21]>O1CCOCC1.[Cu]I>[I:10][C:18]1[CH:21]=[N:20][CH:15]=[C:14]([N+:13]#[C-:12])[CH:19]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 7367935-BromonicotinonitrileHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 125501637HCID 125501637, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To the reaction mixture of 5-bromo-3-cyanopyridine (3 g, 15.9 mmol, 1 eq), sodium iodide (4.77 g, 2 eq), copper(I) iodide (303 mg, 0.1 eq) in anhydrous 1,4-dioxane (40 mL) under nitrogen atmosphere was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.52 mL, 0.2 eq). After the reaction mixture was heated at 120° C. for 16 hours, it was cooled to room temperature and partitioned between aqueous ammonium chloride and ethyl acetate. The organic layer was isolated, washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium chloride. The upper clear solution was decanted, concentrated, and the brown oily residue was subject to a column chromatography (EtOAc-Hex 1:15 to 1:4) yielding 3-iodo-5-isocyanopyridine as a white solid in the amount of 2.41 g.

Workup

  1. temperatureit was cooled to room temperature
  2. custompartitioned between aqueous ammonium chloride and ethyl acetate
  3. customThe organic layer was isolated
  4. washwashed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried with anhydrous sodium chloride
  6. customThe upper clear solution was decanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1a2441623118495abe9652e1df8db72d
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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