3-broMo-2-cyclopropylpyridine synthesis

Yield:944718-27-8 33.5%

Reaction Conditions:

with potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct in lithium hydroxide monohydrate;acetonitrile at 80; for 72 h;

Steps:

1221

Example 1221 Compound 1221A (1.0g, 4.22 mmol), cyclopropyl boronic acid (326 mg, 3.80 mmol) and [PdCI₂(dppf)]CH₂CI₂ (150, 0.21 mmol) in CH₃CN (15 mL) was treated with potassium carbonate (5 mL, 5 mmol, 1 M in H₂O). The mixture was subjected to vacuum and refilled with Nitrogen three times. The reaction mixture was stirred at 80 ⁰C (oil bath) for 3 days. Additional [PdCl₂(dppf)]CH₂CI₂ (150 mg) was added in day two. After cooling down, the water layer was separated and extracted with EtOAc (20 mL) once. The organic layers were combined, filtered through a Celite pad, and concentrated. The product was purified by silica gel chromatography (Hexane/EtOAc, 1 :0 to 10:1 to 5:1) to give 1221B (280 mg, 33.5%)

References:

WO2007/84451,2007,A1 Location in patent:Page/Page column 158