Diphenyl Ether → 2-bromofuro[3,2-c]pyridin-4(5H)-one

Temperature

225 °C

A mixture of 3-(5-bromo-2-furyl)acryloyl azide (20.7 g), diphenyl ether (200 mL) and tributylamine (16 mL) was stirred at 220-230° C. for 30 min under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and tert-butyl methyl ether (200 mL) was added thereto. The resulting solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (hexane, then ethyl acetate/THF), followed by HPLC (C18, mobile phase: water/acetonitrile (including 0.1% TFA)). To the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated in vacuo, and recrystallized from ethyl acetate to give the title compound (7.00 g) as a white solid.

1. temperatureto cool to room temperature
2. filtrationThe resulting solid was collected by filtration
3. customThe obtained solid was purified by silica gel column chromatography (hexane
4. additionTo the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution
5. extractionthe mixture was extracted with ethyl acetate
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. concentrationconcentrated in vacuo
8. customrecrystallized from ethyl acetate

ORD record

ord-1f8700ff20c5490587bd53da5f61a458

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440987B2