Heteroaryl ethers by oxidative palladium catalysis of pyridotriazol-1-yloxy pyrimidines with arylboronic acids.
The oxidative palladium-catalyzed cross-coupling of pyrimidines containing pyridotriazol-1-yloxy (OPt) as either a urea or an amide functional group with arylboronic acids in the presence of Cs(2)CO(3) in DME containing 0.6-1.0% H(2)O is described for the preparation of heteroaryl ethers. The bromo substitution in the case of 3-(5-bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine 1 could serve as a handle for further elaborations such as Suzuki coupling for attaching varied aryl groups.
Bardhan
Sujata
S
Chemical Sciences, Wyeth Research, 401 North Middletown Road, Pearl River, New York 10965, USA.
Wacharasindhu
Sumrit
S
Wan
Zhao-Kui
ZK
Mansour
Tarek S
TS
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
C544034:3-(5-bromo-pyrimidin-2-yloxy)-3H-(1,2,3)triazolo(4,5-b)pyridine; D001897:Boronic Acids; D004987:Ethers; D011725:Pyridines; D011743:Pyrimidines; D014230:Triazoles; D010165:Palladium