Toluene → 5-(4-Bromo-2,3-difluorophenyl)pyrazin-2-amine

Temperatur

80 °C

A mixture of (4-bromo-2,3-difluorophenyl)boronic acid (400 mg, 1.69 mmol) and 5-bromopyrazin-2-amine (588 mg, 3.38 mmol was suspended in EtOH (5.6 ml) and toluene (5.7 mL) The resulting mixture was treated with aqueous Na2CO3 (2.0 N, 4.2 mL, 8.45 mmol). The resulting mixture was then sparged with nitrogen through the mixture for 10 min, and then Pd(PPh3)4 (98 mg, 0.085 mmol) was added. The reaction vessel was sealed and heated at 80° Celsius for 17 hours. The reaction mixture was cooled to rt and then partitioned between saturated aqueous NH4Cl and EtOAc. The organic layer was dried over MgSO4 and concentrated to dryness. The residue was suspended in DCM and the solid isolated by filtration to afford the title compound (160 mg, 33%), which was used without further purification. MS (ESI): mass calcd. for C10H6BrF2N3, 284.97; m/z found, 286.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), 8.01 (d, J=1.2, 1H), 7.68-7.56 (m, 2H), 6.87 (s, 2H).

1. customThe resulting mixture was then sparged with nitrogen through the mixture for 10 min
2. customThe reaction vessel was sealed
3. temperatureThe reaction mixture was cooled to rt
4. custompartitioned between saturated aqueous NH4Cl and EtOAc
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated to dryness
7. customthe solid isolated by filtration

ORD-Eintrag

ord-c9ff847c0a10429a83780defe80b96f5

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09079866B2