Method for manufacturing amino-aryl alkyl compounds

摘要

Preparation of an aminoarylalkyl compound (I) or its salt, comprises reacting an aryl compound (II) with a metallic compound (III) in presence of at least an iron source. Preparation of an aminoarylalkyl compound of formula (R 1>-NH-Aryl-R 2>) (I) or its salt, comprises reacting an aryl compound of formula (R1a-N(R 7>)-Aryl-X) (II) with a metallic compound of formula (R 2>-MeY 1>) (III) in presence of at least an iron source. R 1> : COOR 3>, SO 2-R 4>, SO 2-NH-(1-10C-alkyl), SO 2-NH-(7-15C-arylalkyl), SO 2NH-(6-24C-aryl) or SO 2(NR 5>R 6>); either R 3>, R 4> : 1-10C-alkyl, 2-10C-alkenyl, 1-10C-perhaloalkyl, 7-15C-arylalkyl or 6-24C-aryl; or R 3>R 4> : 1-10C-alkyl or 6-24C-aryl (optionally substituted by 1-10C-alkoxy, Cl, Br or F); either R 5>, R 6> : 1-10C-alkyl; or NR 5>R 6> : a 5-7-membered ring; Aryl : carbocyclic 6-24C-aryl or heteroaryl 3-16C-heteroaryl (all optionally substituted); R 2> : 1-10C-alkyl, 2-10C-alkenyl, 6-24C-aryl, 7-15C-arylalkyl, 3-16C-heteroaryl or 3-7-membered optionally saturated heterocycle (optionally substituted by 1-10C-alkyl, 2-10C-alkenyl, 1-10C-alkoxy, 1-10C-perhaloalkyl, 2-10C-alkynyl, 6-24C-aryl, 3-16C-heteroaryl, COO-(1-10C-alkyl), COO-(7-15C-arylalkyl), OCOO-(1-10C-alkyl), OCOO-(7-15C-arylalkyl), OCOO-(6-24C-aryl), SO 2-(7-15C-arylalkyl), SO 3-(7-15C-arylalkyl), SO 3(6-24C-aryl), SO 3(1-10C-alkyl), COO-(6-24C-aryl), SO 2(1-10C-alkyl), SO 2(6-24C-aryl), CO-(1-10C-alkyl), CO-(6-24C-aryl), SO 2-NH-(1-10C-alkyl), SO 2-NH-(7-15C-arylalkyl), SO 2NH-(6-24C-aryl), SO 2-(NR 9>R 10>), 1-8C-mono- or di-alkylamino, halo, OCO-(NR 11>R 12>) or CO-(NR 11>R 12>)); either R 9>, R 10> : 1-10C-alkyl or 6-24C-aryl; or NR 9>R 10> : 5-7-membered ring; either R 11>, R 12> : 1-10C-alkyl or 6-24C-aryl; or NR 11>R 12> : 5-7 membered ring; R 7> : COOR 3>or SO 2-R 4>; X : Cl, Br, I or -OSO 2-R 8>; R 8> : 1-10C-alkyl, 1-10C-perhaloalkyl, 7-15C-arylalkyl or 6-24C-aryl (all completely substituted by 1-10C-alkoxy, Cl, Br or F); R1a : SO 2-NH-(1-10C-alkyl), SO 2-NH-(7-15C-arylalkyl), SO 2NH-(6-24C-aryl) or SO 2(NR 5>R 6>); and Y 1> : anionic ligand; and Me : Mg, Ca, Mn or Zn. An independent claim is included for the preparation of an amine-aryl compound of formula (IV) or its salt, comprising either converting (I) in the presence of an acid or a base, or (a) reacting an amine-aryl compound of formula (V) with a compound of formula (R 1>-Z) (IV) to obtain an aryl compound of formula (W 1>-Aryl-X) (VII), (b) reacting (VII) to obtain (III) in the presence of an iron source to obtain (I), and (c) converting (I) in the presence of an acid or a base. Z : -O-CO 2-(1-10C-alkyl), -OCO 2(6-24C-aryl), -O-CO 2-(7-15C-arylalkyl), -OSO 2(1-10C-alkyl), -OSO 2(6-24C-aryl), -OSO 2-NH-(7-15C-arylalkyl) or -OSO 2-(7-15C-arylalkyl) (all optionally substituted), F, Cl, Br or I; and W 1> : NHR 1>or N(R 1>) 2.