title: Syntheses of beta,beta-difluorotryptamines.
abstract: Tryptamines disubstituted at the beta-position with fluorine have been synthesized as part of our research program to study the effects of fluorine substitution on the biological activities of neuroactive amines. Treatment of N-Boc-3-azidoacetyl indoles, prepared from readily available 2-chloracetylindoles, with dimethoxyethylamino sulfurtrifluoride produced the corresponding 3-(2-azido-1,1-difluoroethyl)indoles. Reduction of the azide to amine with hydrogen over Pd-C and careful removal of the N-Boc protecting group produced beta,beta-difluorotryptamines.
authors.affiliation: Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, Maryland 20892, USA.
authors.forename: Wei-Ping
authors.initials: WP
authors.lastname: Deng
authors.forename: Ghilsoo
authors.initials: G
authors.lastname: Nam
authors.forename: Junfa
authors.initials: J
authors.lastname: Fan
authors.forename: Kenneth L
authors.initials: KL
authors.lastname: Kirk
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005563:Formic Acid Esters / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000138:chemical synthesis*
chemical_list: D005563:Formic Acid Esters; D006845:Hydrocarbons, Fluorinated; D014363:Tryptamines; C000345:t-butyloxycarbonyl group