(4-Methoxyphenyl)boronic acid → 5-Bromo-N-(4-methoxyphenyl)pyrazin-2-amine

Into a 50 mL roundbottom flask, was placed 4-methoxyphenylboronic acid (5.4 g, 35.54 mmol). To this was added 5-bromo-pyrazin-2-ylamine (3 g, 17.24 mmol). Cu(OAc)2 (3.45 g, 19.06 mmol) was added, followed by addition of a solution of DMAP (4.2 g, 34.43 mmol) in CH2Cl2 (20 mL). The resulting solution was stirred at room temperature for 12 hours. The reaction progress was monitored by thin layer chromatography (TLC) (ethyl acetate/petroleum ether=1:2). When the reaction was complete, the mixture was filtered, then concentrated under vacuum. The residue was dissolved in ethyl acetate (EtOAc), then washed with water. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by silica gel chromatography (SGC) eluting with ethyl acetate/petroleum ether (1:5, v/v) to provide (5-bromo-pyrazin-2-yl)-(4-methoxy-phenyl)-amine (i) (500 mg, yield 10%) as a yellow solid.

1. customInto a 50 mL roundbottom flask, was placed
2. filtrationthe mixture was filtered
3. concentrationconcentrated under vacuum
4. dissolutionThe residue was dissolved in ethyl acetate (EtOAc)
5. washwashed with water
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified by silica gel chromatography (SGC)
10. washeluting with ethyl acetate/petroleum ether (1:5

ORD record

ord-afbe29897df64433a50ef05dad9648c2

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324219B2