Diiodomethane → 4-Cyclopropyl-3-iodopyridine

HRID 572420Notes

Reaction equation

HRID 572420 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 668018874-Cyclopropyl-3-iodopyridineYield 34%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-12119c39bff74fb68d0caef4eaf21003
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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