Sodium Iodide → 3-Iodo-5-phenylethynylpyridine

HRID 606840Notes

Reaction equation

HRID 606840 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[I-:16].[Na+].CNCCNC>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[I:16][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 670476693-Bromo-5-phenylethynylpyridine

Product 1

HCID 670474843-Iodo-5-phenylethynylpyridineYield 81%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 3-bromo-5-phenylethynylpyridine (5.71 g, 22.12 mmol), (prepared essentially as described in EXAMPLE 9), copper (I) iodide (211 mg, 1.1 mmol), sodium iodide (6.63 g, 44.24 mmol) and N,N′-dimethylethylenediamine (0.24 mL, 2.21 mmol) in 1,4-dioxane (20 mL) at 110° C. for 60 h. Cool to room temperature, dilute with ethyl acetate and wash with a saturated aqueous solution of sodium chloride, and dry (sodium sulfate). Purify the residue by silica gel chromatography, eluting with 15:1 hexanes:ethyl acetate, to give the title compound (5.45 g, 81%).

Workup

  1. temperatureHeat
  2. custom(prepared essentially
  3. customat 110° C.
  4. customfor 60 h
  5. washwash with a saturated aqueous solution of sodium chloride
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue by silica gel chromatography
  8. washeluting with 15:1 hexanes

Sources & evidence

ORD record
ord-b76a5c9589a44a07bc98be457ac0e656
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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