Diiodomethane → 4-Cyclopropyl-3-iodopyridine

Participants

Reaction Conditions

Reaction Steps

Isoamyl nitrite (2.62 gm, 22.38 mmol) was added to a stirred solution of 4-cyclopropylpyridin-3-amine (I-73b: 1.0 gm, 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 gm, 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).

Provenance & Evidence