Further metalations and functionalizations of chloro-, bromo- and iodo(trifluoromethyl)pyridines
In accordance with the concept of regioexhaustive functionalization, both 3-chloro-2-(trifluoromethyl)pyridine and 2-bromo-6-(trifluoromethyl)pyridine were converted each time into the three possible carboxylic acids. 2-Bromo-4-(trifluoromethyl)pyridine, 2-bromo-5-(trifluoromethyl)pyridine, 2-iodo-4-(trifluoromethyl)pyridine, and 4-iodo-2-(trifluoromethyl)pyridine were selectively deprotonated and subsequently carboxylated at the resp. 3-positions. Finally, the N-pivaloyl-protected 2-amino-3-chloro-5-(trifluoromethyl)pyridine was deprotonated at the 4-position and the intermediate trapped with iodine and benzaldehyde. [on SciFinder (R)]
WOS:000222752800015
2004
10
1619
1624
CAN 141:243317
27-16
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie moleculaire et biologique, BCh,Ecole Polytechnique Federale,Lausanne,Switz.
Journal
written in English.
100-52-7 (Benzaldehyde); 3282-30-2 (Pivaloyl chloride); 77332-89-9 (3-Chloro-2-iodopyridine); 79456-26-1 (2-Amino-3-chloro-5-(trifluoromethyl)pyridine); 81290-20-2 (Trimethyl(trifluoromethyl)silane); 175205-81-9 (2-Bromo-4-(trifluoromethyl)pyridine); 189278-27-1; 326894-74-0; 430454-70-9; 436799-32-5; 590371-73-6 Role: RCT (Reactant), RACT (Reactant or reagent) (metalations and functionalizations of chloro-, bromo-, and iodo(trifluoromethyl)pyridines); 749875-03-4P; 749875-04-5P; 749875-08-9P; 749875-09-0P; 749875-12-5P; 749875-30-7P; 749875-31-8P; 749875-32-9P (3-Chloro-2-(trifluoromethyl)pyridine) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (metalations and functionalizations of chloro-, bromo-, and iodo(trifluoromethyl)pyridines); 749875-02-3P; 749875-05-6P; 749875-06-7P; 749875-07-8P; 749875-11-4P; 749875-13-6P; 749875-15-8P; 749875-16-9P; 749875-17-0P; 749875-19-2P; 749875-21-6P; 749875-23-8P Role: SPN (Synthetic preparation), PREP (Preparation) (metalations and functionalizations of chloro-, bromo-, and iodo(trifluoromethyl)pyridines)
REVIEWED
EPFL