Sodium Iodide → 5-Iodo-3-methylpyridin-2-amine

HRID 1271056Notes

Reaction equation

HRID 1271056 reaction equation
O1CCOCC1.Br[C:8]1[CH:9]=[C:10]([CH3:15])[C:11]([NH2:14])=[N:12][CH:13]=1.[I-:16].[Na+].CC(C)(N)C(C)(C)N>[Cu](I)I.O>[I:16][C:8]1[CH:9]=[C:10]([CH3:15])[C:11]([NH2:14])=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 312751,4-DioxaneHCID 1233902,3-Butanediamione, 2,3-dimethyl-HCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 9595865-Iodo-3-methylpyridin-2-amineYield 93%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To dioxane (10 mL) was added 5-bromo-3-methylpyridin-2-amine (2 g, 10.6 mmol), sodium iodide (3.2 g, 21.4 mmoL), copper iodide (0.190 g, 1.06 mmol) and the solution degassed followed by addition of tetramethylethane-1,2-diamine (0.803 mL, 1.06 mmol) this mixture heated at 110° C. overnight. After cooling water was added and extracted the crude product with ethyl acetate. The residue was purified by column chromatography to give 5-iodo-3-methylpyridin-2-amine as a beige solid (2.3 g, 93%).

Workup

  1. customthe solution degassed
  2. additionwas added
  3. extractionextracted the crude product with ethyl acetate
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-43d6e3a73cb3456fbaf97377735b77fa
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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