Potassium Carbonate → HCID 10286020, Verbindung

Temperatur

70 °C

A solution of 2-(4-bromo-1H-pyrazol-1-yl)pyridine (0.669 g, 3 mmol), 3-chlorophenylboronic acid (0.468 g, 3 mmol) and potassium carbonate (0.828 g, 6 mmol) in a mixture of ethyleneglycol dimethyl ether (20 mL) and H2O (4 mL) were degassed by argon bubbling for 15 min., then tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) was added and degasing continued a further 15 min. The solution was stirred at 70° C. for 14 h, whereupon H2O (30 mL) was added, then extracted with EtOAc (3×30 mL) and the combined extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and the crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4) to afford a white solid which was recrystallized from EtOAc/Hexane to give 2-[4(3-chlorophenyl)-1H-pyrazol-1-yl]pyridine. MP=110-111° C. 1H NMR (CD3Cl, 300 MHz) δ 8.83 (d, 1H), 8.42 (dd, 1H), 7.99 (s, 1H), 7.99 (d, 1H), 7.82 (ddd, 1H), 7.57 (t, 1H), 7.45 (dt, 1H), 7.32 (t, 1H), 7.25˜7.18 (m, 2H). MS (ESI) 255.9 (M++H).

1. customwere degassed by argon bubbling for 15 min.
2. customdegasing
3. additionwas added
4. extractionextracted with EtOAc (3×30 mL)
5. washthe combined extracts washed with brine
6. dry with materialThe organic phase was dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customthe crude residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4)
9. customto afford a white solid which
10. customwas recrystallized from EtOAc/Hexane

ORD-Eintrag

ord-ae1d7f89507c4508b6e5083c2c2ba2c0

Quelldatensatz

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07569592B2