• 专利标题:   Preparing amine intermediate comprises treating the 3-iodo-1H-pyrazolo(3,4-d)pyrimidin-4-amine derivatives with 4-phenoxybenzene boronic acid in the presence of graphene-nickel/palladium used as catalyst and strong base in solvent.
  • 专利号:   WO2020117135-A1
  • 发明人:   HAAS P D, STECKEL A H, BELLUR ATICI E, ALTUNDAS R, OZTURK AYDIN B, SECEN H, AYDIN B N
  • 专利权人:   DEVA HOLDING AS
  • 国际专利分类:   C07D471/04
  • 专利详细信息:   WO2020117135-A1 11 Jun 2020 C07D-471/04 202051 Pages: 20 English
  • 申请详细信息:   WO2020117135-A1 WOTR050761 04 Dec 2018
  • 优先权号:   WOTR050761

▎ 摘  要

NOVELTY - Preparing amine intermediate (I) comprises treating the 3-iodo-1H-pyrazolo(3,4-d)pyrimidin-4-amine derivatives (III) with 4-phenoxybenzene boronic acid (II), in the presence of G-Ni/Pd used as catalyst and a strong base in a solvent to obtain (I). USE - The process is useful for preparing amine intermediate (I), which is used in synthesis of ibrutinib (all claimed). ADVANTAGE - The process: is simple cost-effective and safe; provides excellent yields and purity with (lower cost, low toxicity, commercial availability of large number of boronic acids, excellent functional group tolerance and good availability of diverse organoboron reagents that are stable in air); and provides high quality ibrutinib intermediates would be also helpful for patients to get access to affordable and cheap ibrutinib drug products. DETAILED DESCRIPTION - Preparing amine intermediate of formula (I) comprises treating the 3-iodo-1H-pyrazolo(3,4-d)pyrimidin-4-amine derivatives of formula (III) with 4-phenoxybenzene boronic acid of formula (II), in the presence of graphene-nickel/palladium used as catalyst and a strong base in a solvent to obtain (I). X1 = H or N-(tert-butoxycarbonyl)piperidine.