title: C-6 regioselective bromination of methyl indolyl-3-acetate.
abstract: An efficient route to natural occurring methyl 6-bromoindolyl-3-acetate 1c from methyl indolyl-3-acetate 3 was achieved in 3 steps and 68% overall yield. Thus, in order to regioselectively brominate 3 at the C6-position, introduction of electron withdrawing substituents at N1 and C8 was affected to give intermediate 4 in 82% yield. Bromination of 4 with 8 equiv of bromine in CCl4 and washings with aqueous Na2SO3 gave 5 in 86% yield, which was N- and C-decarbomethoxylated by treatment with NaCN in DMSO, affording 1c in 97% yield. The regioselectivity of bromination was evidenced by NMR spectroscopy and X- ray diffraction analysis.
authors.affiliation: Area Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184 México. osuarez@uaeh.edu.mx
authors.forename: Oscar R
authors.initials: OR
authors.lastname: Suárez-Castillo
authors.forename: Myriam
authors.initials: M
authors.lastname: Meléndez-Rodríguez
authors.forename: Lidia
authors.initials: L
authors.lastname: Beiza-Granados
authors.forename: Indira C
authors.initials: IC
authors.lastname: Cano-Escudero
authors.forename: Martha S
authors.initials: MS
authors.lastname: Morales-Ríos
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: D000085:Acetates / Q000737:chemistry*; D054879:Halogenation; D007211:Indoles / Q000737:chemistry*
chemical_list: D000085:Acetates; D007211:Indoles