title: Synthesis of a key intermediate for the preparation of FTY720 analogs.
abstract: A concise synthesis of a useful intermediate 10 for the preparation of fingolimod (FTY-720) analogs was achieved by utilizing a chemoselective Sonogashira reaction of trihalobenzene 12 with alkyne 13. The reaction proceeded with high selectivity to give alkyne 11 containing the dihalobenzene moiety in good yield. Compound 11 was converted into intermediate 10 by hydrogenation without reduction of the halogen atoms.
authors.affiliation: School of Pharmaceutical Science, Toho University, Funabashi, Chiba 274–8510, Japan. hamada.maiko@mc.mt-pharma.co.jp
authors.forename: Maiko
authors.initials: M
authors.lastname: Hamada
authors.forename: Kunitomo
authors.initials: K
authors.lastname: Adachi
authors.forename: Hidemasa
authors.initials: H
authors.lastname: Hikawa
authors.forename: Yuusaku
authors.initials: Y
authors.lastname: Yokoyama
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D000068876:Fingolimod Hydrochloride; D007166:Immunosuppressive Agents / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011409:Propylene Glycols / Q000138:chemical synthesis / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000480:Alkynes; D001555:Benzene Derivatives; D007166:Immunosuppressive Agents; C501899:KRP-203; D011409:Propylene Glycols; D013438:Sulfhydryl Compounds; D010165:Palladium; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine