Syntheses of beta,beta-difluorotryptamines.
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.
Deng
Wei-Ping
WP
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.
Nam
Ghilsoo
G
Fan
Junfa
J
Kirk
Kenneth L
KL
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*
D005563:Formic Acid Esters; D006845:Hydrocarbons, Fluorinated; D014363:Tryptamines; C000345:t-butyloxycarbonyl group