hydroxylamine-O-sulfonic acid → 7-iodo-[1,2,4]triazolo[1,5-a]pyridine

Temperature

130 °C

To a stirred solution of the product from Step B above (220 mg, 1.00 mmol) in N,N-dimethylformamide (0.5 mL) was added N,N-dimethylformamide dimethyl acetal (0.37 mL, 2.60 mmol). The reaction mixture was heated to 130° C. overnight. After cooling to room temperature, the volatiles were removed under reduced pressure to afford a red oil, which was dissolved in 2.0 mL of methanol and 0.162 mL of pyridine. The solution was cooled in an ice bath and hydroxylamine-O-sulfonic acid (147 mg, 1.30 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The volatiles were removed under reduced pressure, and the residue was partitioned between saturated aqueous brine solution and ethyl acetate. The aqueous layer was further extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous brine solution (100 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as an orange solid. MS 246.1 (M+1).

1. temperatureAfter cooling to room temperature
2. customthe volatiles were removed under reduced pressure
3. customto afford a red oil, which
4. temperatureThe solution was cooled in an ice bath
5. temperatureto warm to room temperature
6. customThe volatiles were removed under reduced pressure
7. customthe residue was partitioned between saturated aqueous brine solution and ethyl acetate
8. extractionThe aqueous layer was further extracted with ethyl acetate
9. washthe combined organic layers were washed with saturated aqueous brine solution (100 mL)
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated under reduced pressure

ORD record

ord-13c1eb2eb5ad4efa82cd645194c34b17

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157490B2