Water → HCID 18446635, compound

To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-pyridinyl)ethanone oxime (6.0 g, 24 mmol) in 1,2-dimethoxyethane (40 mL) at 0° C. was added trifluoroacetic anhydride (3.4 mL, 24 mmol), keeping the temperature below 10° C. during the addition. After the addition was complete, the reaction was warmed to room temperature. The solution was then cooled to 4° C. and a solution of triethylamine (6.7 mL, 48 mmol) in 1,2-dimethoxyethane (15 mL) was added over a period of 0.5 hours. The mixture was allowed to warm to room temperature and was stirred for 1.5 hours. To this mixture was added iron(II) chloride (50 mg) and the reaction was heated at 75° C. for 15 hours. The reaction mixture was poured into water (300 mL). The resulting suspension was extracted with ethyl acetate. The ethyl acetate phase was dried (magnesium sulfate), filtered and concentrated to a solid residue. This residue was purified by silica gel chromatography (1:1 ethyl acetate-hexane) to give 7-chloro-2-(4-pyridinyl)pyrazolo[1,5-a]pyridine (2.8 g, 500%) as a tan solid. 1H NMR (d6-DMSO): δ 8.62 (m, 2H), 7.93 (m, 2H), 7.76 (dd, 1H), 7.42 (m, 2H), 7.24 (m, 1H); MS m/z 230 (M+1).

1. customthe temperature below 10° C.
2. additionduring the addition
3. additionAfter the addition
4. temperatureThe solution was then cooled to 4° C.
5. temperatureto warm to room temperature
6. temperaturethe reaction was heated at 75° C. for 15 hours
7. extractionThe resulting suspension was extracted with ethyl acetate
8. dry with materialThe ethyl acetate phase was dried (magnesium sulfate)
9. filtrationfiltered
10. concentrationconcentrated to a solid residue
11. customThis residue was purified by silica gel chromatography (1:1 ethyl acetate-hexane)

ORD record

ord-2bf05687f9924b0ba6f7de959f8cd8d3

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199120B2