Solid-phase synthesis of 4-biaryl-piperidine-4-carboxamides

Tetrahedron Letters

Volumn 47, Issue 40, 2006, Pages 7267-7270

  Zhu, Jin ^a   Pottorf, Richard S ^a   Player, Mark R ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Biaryl piperidine; Solid phase; Suzuki coupling

Indexed keywords

AMIDE; RESIN;

ARTICLE; CHEMICAL REACTION; SOLID PHASE SYNTHESIS;

EID: 33747881275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.070     Document Type: Article

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11. +).
12. 3 (2 M, 20 equiv), and boronic acid (10 equiv). The mixture was flushed with argon, and the reaction vessel was then sealed. The reaction vessel was heated at 75 °C for 20 h. The resin was washed with water, DMF, MeOH, DCM, and MeOH, and then dried in vacuo overnight. Cleavage of product from the resin: The resin was treated with 10% TFA in DCM for 30 min. After the solvent was evaporated, the compounds were analyzed with proton NMR and LC-MS. The LC-MS instrument was equipped with an analytical HPLC column and a UV detector in determining the purity of the products. NMR data was also collected on the crude products. To further confirm on the yield and purity of the products, a small set of compounds (out of those in Table 1) were purified. The yields of the purified compounds were consistent with the reported yields of the crude products.