5-Bromo-2-furanecarboxylic acid → HCID 18472462, compound

To a suspension of 5-bromo-2-furancarboxylic acid (5.00 g) and N-hydroxysuccinimide (3.31 g) in acetonitrile (50 ml) was added 1-ethyl-3—(3′-dimethylaminopropyl)-carbodiimide hydrochloride (5. 52 g) at room temperature, and the mixture was stirred for 2 hours. To the reaction mixture was added a suspension of N,O-dimethylhydroxyl-amine hydrochloride (2.81 g) and triethylamine (10 ml) in acetonitrile (20 ml), and the mixture was stirred for 1 hour. To the reaction mixture were added 1,8-diazabicyclo-[5.4.0]-7-undecene (4.3 ml) and DMF (50 ml), and the mixture was stirred for 3 hours and concentrated under reduced pressure. To the residue was added water, and the mixture was extraeted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:4→1:3→1:2) to give N-methyl-N-methoxy-5-bromofuran-2-carboxamide (2.77 g) as pale yellow oil.

1. additionTo the reaction mixture was added
2. stirringthe mixture was stirred for 1 hour
3. stirringthe mixture was stirred for 3 hours
4. concentrationconcentrated under reduced pressure
5. additionTo the residue was added water
6. washThe organic layer was washed with saturated sodium chloride solution
7. dry with materialdried with magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was separated
10. custompurified with column chromatography (ethyl acetate/hexane=1:4→1:3→1:2)

ORD record

ord-6a5073dab4774fb4ac9e3e40d3c18086

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413947B1