Ethyl Acetate → HCID 10171469, Verbindung

Temperatur

84 °C

2-(3-Bromo-1H-pyrrol-1-yl)pyridine (1.34 g, 2 mmol), 3-methoxyphenylboronic acid (0.61 g, 4 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol) and potassium carbonate (560 mg, 4 mmol) were dissolved in a mixture of DME (18 mL) and H2O (2 mL) and degassed for 15 min with Ar (g). The reaction mixture was then heated at 84° C. for 18 h. At this time, a further 0.25 eq. of 3-methoxyphenylboronic acid (0.15 g, 1 mmol) was added and heating was continued. After a total of 42 h, the reaction mixture was cooled to rt, H2O (40 mL) and EtOAc (40 mL) were added and the reaction mixture shaken, the EtOAc layer was separated and the aqueous layer shaken with EtOAc (2×30 mL). The combined organic layers were dried over Na2SO4 and concentrated to a yellow oil. This was purified by liquid chromatography on silica gel eluting with EtOAc:hexane (3:7) to afford a white solid that was further purified by preparative HPLC to afford 2-[3-(3-methoxyphenyl)-1H-pyrrol-1-yl]pyridine as a white solid. 1H NMR (CD3Cl, 300 MHz) δ 8.52-8.54 (1H, m), 7.55 (1H, ddd), 7.38-7.39 (1H, m), 7.15-7.21 (2H, m), 6.76-6.85 (4H, m), 6.46-6.48 (1H, m), 6.41 (1H, dd). MS (ESI) 251 (M+H)+.

1. customdegassed for 15 min with Ar (g)
2. temperatureheating
3. temperatureAfter a total of 42 h, the reaction mixture was cooled to rt
4. customthe EtOAc layer was separated
5. stirringthe aqueous layer shaken with EtOAc (2×30 mL)
6. dry with materialThe combined organic layers were dried over Na2SO4
7. concentrationconcentrated to a yellow oil
8. customThis was purified by liquid chromatography on silica gel eluting with EtOAc:hexane (3:7)
9. customto afford a white solid
10. customthat was further purified by preparative HPLC

ORD-Eintrag

ord-fca95bdc7a5e4d95b7ee955cee3ea8bd

Quelldatensatz

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07371767B2