Fluoroboron compound, aminomethylating agent for aromatic ring made of the same, and production method of compound containing aminomethyl aromatic ring using aminomethylating agent
AssigneeEisai R&D Management Co., Ltd.
InventorKeigo Tanaka
Life of this patent
Estimating the term…
Abstract
A production method of a compound containing a primary, secondary, or tertiary aminomethyl aromatic ring of the present invention includes: using a fluoroboron compound or a dimer thereof, or solvates thereof, which are represented by a formula (I): Ra(Rb)N—CH2—BF3M (I) as an aminomethylating agent for an aromatic ring; and reacting the aminomethylating agent with an aromatic ring-containing compound, which can react with the aminomethylating agent, under the presence of a metal catalyst such as a palladium compound so as to perform the direct aminomethylation of the aromatic ring.
Claims5
A fluoroboron compound or a dimer of the fluoroboron compound, or solvates of the fluoroboron compound and the dimer, the fluoroboron compound being represented by a formula (I):
- Ra(Rb)N—CH2—BF3M (I)
- wherein Ra and Rb each independently represents a group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a protecting group of an amino group, a protecting group of an amino group formed by joining a nitrogen atom bonded with Ra and Rb and a substituted or unsubstituted heterocyclic group, which may contain 1 or more heteroatoms by an optional choice, formed by joining a nitrogen atom bonded with Ra and Rb, and
- M represents an alkali metal cation, and
- wherein potassium n-butylaminomethyl trifluoroborate, potassium cyclohexylaminomethyl trifluoroborate, potassium N-pyrrolidinylmethyl trifluoroborate, and potassium N-piperidylmethyl trifluoroborate are excluded from formula (I), and
- wherein substituted means a substituent group is attached selected from:
- halogen, amino, mono- or di-alkylamino, nitro, cyano, C1-6 alkyl, C1-6 alkoxy, and C3-8 cycloalkyl, and
- wherein heterocyclic group means a non-aromatic hydrocarbon cyclic group having 1 or more heteroatoms.
Dependencies are inferred from the claim text.