Cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines: synthesis of hyrtinadine A.
The palladium-catalyzed cross-coupling reaction of triorganoindium reagents (R3In) with 5-bromo-2-chloropyrimidine proceeds chemoselectively, in good yields, to give 5-substituted-2-chloropyrimidines or 2,5-disubstituted pyrimidines using 40 or 100 mol % of R3In, respectively. Sequential cross-couplings are also performed, in one pot, using two different R3In. This method was used to achieve the first synthesis of the alkaloid hyrtinadine A. The key step was a two-fold cross-coupling reaction between a tri(3-indolyl)indium reagent and 5-bromo-2-chloropyrimidine.
Mosquera
Angeles
A
Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain
Riveiros
Ricardo
R
Pérez Sestelo
José
J
Sarandeses
Luis A
LA
D007204:Indium / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*
D026121:Indole Alkaloids; D009942:Organometallic Compounds; D011743:Pyrimidines; C519139:hyrtinadine A; D007204:Indium