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US 10,323,033 B2Granted
Imidazo[1,2-A]pyridine-3-carboxylate derivative and preparation method thereof
AssigneeKnu-Industry Cooperation Foundation
InventorPhil Ho Lee
Life of this patent
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Abstract
Provided are an imidazo[1,2-a]pyridine-3-carboxylate derivative and a preparation method thereof, and more particularly, a method of effectively preparing an imidazo[1,2-a]pyridine-3-carboxylate derivative by performing an aza-[3+2] cycloaddition reaction of a pyridine derivative with an α-diazo oxime ether derivative in the presence of a copper (II) catalyst, and an imidazo[1,2-a]pyridine-3-carboxylate derivative prepared thereby.
Claims9
A preparation method of an imidazo[1,2-a]pyridine-3-carboxylate derivative comprising:
- performing an aza-[3+2] cycloaddition reaction of a pyridine derivative represented by Chemical Formula 6 below with an α-diazo oxime ether derivative represented by Chemical Formula 7 below in the presence of a copper (II) catalyst, thereby preparing an imidazo[1,2-a]pyridine-3-carboxylate derivative represented by Chemical Formula 1 below:
- in Chemical Formulas 1, 6, and 7,
- R1 is (C1-C10)alkyl, (C6-C12)aryl or (C3-C12)heteroaryl, and the aryl of R1 may be further substituted with one or more selected from the group consisting of (C1-C10)alkyl, halo(C1-C10)alkyl, (C1-C10)alkoxy, halogen, nitro, (C1-C10)alkylcarbonyl, (C1-C10)alkoxycarbonyl and (C6-C12)aryloxy;
- R2 is (C1-C10)alkyl or halo(C1-C10)alkyl;
- R3 is (C1-C10)alkoxy;
- X is CRb or N;
- Y is CRc or N;
- Z is CRd or N;
- Ra to Rd are each independently hydrogen, (C1-C10)alkyl, halo(C1-C10)alkyl, halogen, (C1-C10)alkylcarbonyl, halo(C1-C10)alkylcarbonyl, (C1-C10)alkoxycarbonyl, halo(C1-C10)alkoxycarbonyl, (C6-C12)aryl(C1-C10)alkyloxy, (C6-C12)aryl or (C3-C12)heteroaryl, or may be linked to an adjacent substituent via —CR11═CR12—CR13═CR14— to form a fused ring, and the aryl of Ra to Rd may be further substituted with one or more selected from (C1-C10)alkyl, halo(C1-C10)alkyl, (C1-C10)alkoxy, (C6-C12)aryl and halogen;
- R11 to R14 are each independently hydrogen, (C1-C10)alkyl, halo(C1-C10)alkyl, (C1-C10)alkoxy, (C6-C12)aryl, or halogen;
- and
- the heteroaryl includes one to four heteroatoms selected from N, O and S.
9 more elements
A preparation method of an imidazo[1,2-a]pyridine-3-carboxylate derivative comprising:
- performing an aza-[3+2] cycloaddition reaction of a pyridine derivative represented by Chemical Formula 6A below with an α-diazo oxime ether derivative represented by Chemical Formula 7A below in the presence of a copper (II) catalyst in trifluoroethanol, followed by transesterification with trifluoroethanol as a solvent, thereby preparing an imidazo[1,2-a]pyridine-3-carboxylate derivative represented by Chemical Formula 1A below:
- in Chemical Formulas 1A, 6A, and 7A,
- R1 is (C1-C10)alkyl or (C6-C12)aryl, and the aryl of R1 may be further substituted with one or more selected from the group consisting of (C1-C10)alkyl, (C1-C10)alkoxy, halogen, nitro and (C1-C10)alkoxycarbonyl;
- R2 is (C1-C10)alkyl;
- Y is CRc or N;
- R3 is (C1-C10)alkoxy;
- Ra is hydrogen, (C1-C10)alkyl or (C6-C12)aryl(C1-C10)alkyloxy;
- Rb is (C1-C10)alkyl or (C6-C12)aryl, and the aryl of Rb may be further substituted with one or more selected from (C1-C10)alkyl and halogen;
- and
- Rc is hydrogen or (C1-C10)alkyl.
7 more elements
Dependencies are inferred from the claim text.