[4-(1H-IMIDAZOL-4-YL)-PHENYL]-METHANOL synthesis

Yield:328547-42-8 46%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;N-benzyl-N,N,N-triethylammonium chloride;cesium fluoride in water;toluene at 120; for 1 h;Microwave irradiation;Inert atmosphere;Suzuki-Miyaura Coupling;

Steps:

General procedures for the synthesisof 4(5)-aryl-1H-imidazoles (3)

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl₂(dppf)(0.041 g, 0.05 mmol) and BnEt₃NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

References:

Vichier-Guerre, Sophie;Dugué, Laurence;Pochet, Sylvie [Tetrahedron Letters,2014,vol. 55,# 46,p. 6347 - 6350] Location in patent:supporting information