Anisole → HCID 117770353, compound

N-((6-Bromopyridin-2-yl)methyl)-N-(2,4-dimethoxybenzyl)formamide obtained in Reference Example 20 (830 mg) and anisole (1.0 mL) were dissolved in formic acid (20 mL), and the solution was stirred at 100% for 8 hr. The mixture was allowed to be cooled to room temperature, and concentrated under reduced pressure. The residue was subjected to azeotropy with toluene, to the residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate) to give the title compound (279 mg).

1. concentrationconcentrated under reduced pressure
2. additionto the residue was added saturated aqueous sodium hydrogen carbonate solution
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (basic silica gel, hexane/ethyl acetate)

ORD record

ord-266d0ba8cd5c481c86fafd135ab0c216

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085578B2