Back to results
US 2010/0137588 A1Published application
Method for preparing ortho-substituted aminoferrocenes
AssigneeBrock University
InventorCosta Metallinos
Life of this patent
Estimating the term…
Abstract
The present disclosure relates to a method for preparing an ortho-substituted aminoferrocene comprising reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile to form the ortho-substituted aminoferrocene.
Claims32
A method for preparing an ortho-substituted aminoferrocene comprising:
- (i) reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile under suitable conditions to produce the ortho-substituted aminoferrocene;
- or
- (ii) reacting an aminoferrocene with a Lewis acid and a lithiating reagent under suitable conditions to form a lithiated aminoferrocene and subsequently reacting the lithiated aminoferrocene with an electrophile under suitable conditions to produce the ortho-substituted aminoferrocene.
A compound of the formula (A):
- wherein R1 and R2 are simultaneously or independently selected from C1-10alkyl and C3-10cycloalkenyl, the latter 2 groups being optionally substituted, or R1 and R2 are linked together to form an optionally substituted monocyclic or bicyclic, saturated ring having 4 or more atoms, including the nitrogen atom to which said groups are bonded;
- wherein each R′ and R″ is independently or simultaneously selected from H, fluoro, chloro, (C1-C6)-alkyl or fluoro-substituted-(C1-C6)-alkyl;
- n is 1, 2 or 3;
- m is 1, 2, 3, 4 or 5;
- W is PR3R4, P(Y)R3R4, SiR5R6R7, SnR5R6R7, halo, S—R8, borate esters, CH2heteroaryl, CH2OR9, C6-10aryl, C6-10aryl substituted with one to three halo, C1-10alkyl, OR3, PR3R4 and/or NR5R6, C(O)H, C(OH)R5R6, OR9, C(O)NR9R10 or CH2NR9R10;
- R3 and R4 are simultaneously or independently selected from C1-20alkyl, C3-20cycloalkyl, C6-14aryl and heteroaryl, the latter three groups being optionally substituted, or R3 and R4 are linked together to form an optionally substituted monocyclic or polycyclic, saturated, unsaturated and/or aromatic ring system having 4 or more atoms, including the phosphorous atom to which said groups are bonded, and in which one or more carbon atoms in said monocyclic or polycyclic ring system is optionally replaced with a heteromoiety selected from O, N, NH and N—C1-6alkyl;
- R5, R6, R7 and R8 are simultaneously or independently selected from C1-10alkyl, C2-10alkenyl, C3-10cycloalkyl and C6-10aryl, each being optionally substituted with one to four optional substituents selected from halo, C1-6alkyl, fluoro-substituted C1-6alkyl, C3-6cycloalkyl and phenyl;
- R5, R6, R7 and R8 are simultaneously or independently selected from C1-10alkyl, C2-10alkenyl, C3-10cycloalkyl and C6-10aryl, each being optionally substituted with one to four substituents independently selected from halo, C1-6alkyl, fluoro-substituted C1-6alkyl, C3-6cycloalkyl and phenyl,
- R9 and R19 are simultaneously or independently selected from H, C(O)R8, C1-10alkyl, C2-10alkenyl, C3-10cycloalkyl and C6-10aryl, each being optionally substituted with one to four substituents independently selected from halo, C1-6alkyl, fluoro-substituted C1-6alkyl, C3-6cycloalkyl and phenyl;
- Y is S or O;
- and
- heteroaryl is a 5- or 6-membered ring containing 1 to 5 heteromoieties selected from S, O, N, NH and N—C1-6alkyl;
- or any stereoisomer and/or enantiomer thereof,
- with the proviso that R9 and R19 are not simulataneously C1-10alkyl.
11 more elements
Dependencies are inferred from the claim text.