Potassium Carbonate → 7-bromo-8-(4-chlorophenyl)-2-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Temperature

20 °C

To a degassed mixture of 7-bromo-8-iodo-2-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (3.0 g, 7.8 mmol), 4-chlorophenylboronic acid (1.32 g, 8.6 mmol) and K2CO3 (2.16 g, 15.6 mmol) in 1,4-dioxane (42 mL) and H2O (14 mL) under argon at 20° C. was added Pd(PPh3)4 (450 mg, 0.39 mmol). The reaction mixture was refluxed for 40 h under argon and then cooled to 20° C. The reaction mixture was diluted with H2O (30 mL) and extracted with EtOAc (3×50 mL). The combined organic extract was washed with saturated aqueous NaHCO3 solution (50 mL), then brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was successively triturated with hexanes and Et2O and dried under high vacuum to obtain the title compound as a light yellow solid (2.7 g, 7.4 mmol) in 85% purity along with bis-4-chlorophenyl coupled by-product. The crude product was used without further purification. MS: [M+H]+=368.0.

1. temperatureThe reaction mixture was refluxed for 40 h under argon
2. extractionextracted with EtOAc (3×50 mL)
3. extractionThe combined organic extract
4. washwas washed with saturated aqueous NaHCO3 solution (50 mL)
5. dry with materialbrine (50 mL), dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was successively triturated with hexanes and Et2O
9. customdried under high vacuum

ORD record

ord-11a862de9f6649a5a224528a4d991405

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572808B2