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ChemicalBook CAS DataBase List 8-bromo-6-iodo-[1,2,4]triazolo[1,5-a]pyridine
1415314-10-1

8-bromo-6-iodo-[1,2,4]triazolo[1,5-a]pyridine synthesis

4synthesis methods
Methanimidamide, N'-(3-bromo-5-iodo-2-pyridinyl)-N-hydroxy-, (1Z)-

1415728-06-1
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8-bromo-6-iodo-[1,2,4]triazolo[1,5-a]pyridine

1415314-10-1
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Yield:1415314-10-1 62%

Reaction Conditions:

Stage #1: (E)-N'-(3-bromo-5-iodopyridin-2-yl)-N-hydroxy-formimidamidewith trifluoroacetic anhydride in tetrahydrofuran at 0 - 20;
Stage #2: with sodium hydrogencarbonate in tetrahydrofuran;water; pH=8;

Steps:

7.3

Step 38-Bromo-6-iodo-[1,2,4]-triazolo[1,5-a]pyridine Procedure:To a stirred solution of (E)-N-(3-bromo-5-iodopyridin-2-yl)-N-hydroxyformimidamide (4.2 g, 12.2 mmol) in THF (120 mL) at 0° C. was added dropwise 2,2,2-trifluoroacetic anhydride (10 mmol) slowly. After the addition, the reaction mixture was stirred at room temperature for 24 h. Then the reaction mixture was treated by saturated sodium bicarbonate solution until it reached pH=8. The solvent was evaporated at 40° C. at reduced pressure to give a crude product. This was purified by column chromatography (silica gel, 200-300 mesh, dichloromethane and methanol 100:1.5, v/v) to give 8-bromo-6-iodo-[1,2,4]triazolo[1,5-a]pyridine (2.45 g, 62%) as a pale yellow solid. 1H NMR (300 MHz, CD3OD): δ 9.16 (d, 1H, J=1.2 Hz), 8.38 (s, 1H), 8.20 (d, 1H, J=0.9 Hz). LC/MS: 323.8 [M+H]+.

References:

US2012/309746,2012,A1 Location in patent:Page/Page column 33

20511-12-0 Synthesis
2-Amino-5-iodopyridine

20511-12-0
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8-bromo-6-iodo-[1,2,4]triazolo[1,5-a]pyridine

1415314-10-1
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