Water → HCID 22486277, compound

The synthesis was performed with reference to the known literature (Tetrahedron, Vol. 63, p. 419, 2007). A solution of 1H-indazole-3-carboxaldehyde (0.888 g, 6.08 mmol) in methylene chloride (8 mL) was added with 50% aqueous potassium hydroxide (6 mL) and tetrabutylammonium bromide (0.0196 g, 0.0608 mmol), and the mixture was cooled on ice. The reaction mixture was added dropwise with 2-(trimethylsilyl)ethoxymethyl chloride (1.18 mL, 6.67 mmol), and the mixture was stirred for 1 hour under ice cooling, and then at room temperature overnight. The reaction mixture was added with water (30 mL), and the mixture was extracted three times with methylene chloride. The organic layer was dried over magnesium sulfate, and concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain N-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-3-carboxaldehyde.

1. temperaturethe mixture was cooled on ice
2. customat room temperature
3. customovernight
4. extractionthe mixture was extracted three times with methylene chloride
5. dry with materialThe organic layer was dried over magnesium sulfate
6. concentrationconcentrated
7. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-cde0b90c9f854dddaef6bb1e20a989e7

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156827B2