5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thieno[2,3-b]pyridine synthesis

Yield:-

Reaction Conditions:

with potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane at 85;

Steps:

9.C
A mixture of the product, 5-bromothieno[2,3-b]pyridine_I from Part B (1 equiv), bispinacolatodiboron (1.2 equiv), PdCI₂dppf (0.1 equiv), and potassium acetate (3 equiv) in dioxane was heated at 85 °C until the reaction was deemed complete by TLC, HPLC, or LC-MS analysis. The reaction was allowed to cool to room temperature, filtered through a pad of celite, concentrated to dryness, treated with diethyl ether, filtered through a pad of celite, and then concentrated to afford the desired product, 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thieno[2,3-b]pyridine.

References:

SCHERING CORPORATION;DENG, Yongqi;SUN, Binyuan;ZENG, Hongbo;RICHARDS, Matthew;SHIPPS, Gerald, W., Jr.;CHENG, Cliff, C.;ZHAO, Yinyan;MCRINER, Andrew;MENG, Zhaoyang;NAN, Yang;PATEL, Mehul, F.;WRONA, Iwona, E.;REDDY, Panduranga, Adulla;EKLOV, Brian, M.;TANG, Shuyi;LIU, Duan;MANDAL, Amit, K.;ZHAO, Lianyun;SIDDIQUI, M., Arshad WO2010/118207, 2010, A1 Location in patent:Page/Page column 284-285