Dimethylformamide → HCID 86625547, compound

Temperature

-78 °C

A solution of the compound 6-bromo-1-cyclopentyl-1H-indazole (1.19 g, 4.15 mmol) in dry tetrahydrofuran (10 ml) was stirred at −78° C. for 15 minutes followed by the addition of butyl lithium (0.532 g, 8.3 mmol). The reaction mixture was again stirred for 30 minutes at −78° C. followed by the dropwise addition of dimethylformamide (1.212 g, 16.6 mmol). The reaction mixture was stirred for 30 minutes at the same temperature followed by stirring it at room temperature for 1 hour. The reaction mixture was quenched with hydrochloric acid (1N) and extracted the compound with ethyl acetate and water. The organic layer was collected, washed with brine and dried over anhydrous sodium sulphate. The mixture was filtered and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compound. Yield: 465 mg.

1. stirringThe reaction mixture was stirred for 30 minutes at the same temperature
2. stirringby stirring it at room temperature for 1 hour
3. customThe reaction mixture was quenched with hydrochloric acid (1N)
4. extractionextracted the compound with ethyl acetate and water
5. customThe organic layer was collected
6. washwashed with brine
7. dry with materialdried over anhydrous sodium sulphate
8. filtrationThe mixture was filtered
9. concentrationconcentrated under reduced pressure
10. customThe residue thus obtained
11. customwas purified by column chromatography

ORD record

ord-20921421dc3c420e9e8fe507a2f33a42

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07781460B2