2,2'-Bipyridine → 1-cyclopropyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine

Temperatur

50 °C

To a solution of 6-fluoro-1H-pyrrolo[2,3-b]pyridine (6.2 g, 45.55 mmol) in dry DCM (250 mL) is added cyclopropylboronic acid (7.82 g, 91.09 mmol), followed by cupric acetate (8.36 g, 45.55 mmol), sodium carbonate (9.65 g, 91.09 mmol) and 2,2′-bipyridine (7.11 g, 45.55 mmol). The resulting mixture is stirred and heated at 50° C. for 15 h. The mixture is cooled to room temperature and further cupric acetate (4.18 g, 22.77 mmol) and sodium carbonate (2.41 g, 22.77 mmol) are added, followed by cyclopropylboronic acid (1.96 g, 22.77 mmol). The mixture is stirred and heated at 50° C. for a further 15 h when further cupric acetate (1.5 g, 8.25 mmol) and cyclopropylboronic acid (1.49 g, 17.34 mmol) are added. The mixture is stirred at room temperature for 4 days and then poured onto sat. aq. NH4Cl, diluted with water and extracted with DCM. The organic layers are combined, washed with brine, dried (magnesium sulphate) and concentrated in vacuo to give a green oil, which is purified by column chromatography on silica, eluting with DCM, to give the title compound (2.03 g, 11.52 mmol). MS (m/z): 177 (M+1). Unreacted 6-fluoro-1H-pyrrolo[2,3-b]pyridine is also recovered (3.012 g, 22.1 mmol). MS (m/z): 137 (M+1).

1. temperatureThe mixture is cooled to room temperature
2. stirringThe mixture is stirred
3. additionare added
4. stirringThe mixture is stirred at room temperature for 4 days
5. extractionextracted with DCM
6. washwashed with brine
7. dry with materialdried (magnesium sulphate)
8. concentrationconcentrated in vacuo
9. customto give a green oil, which
10. customis purified by column chromatography on silica
11. washeluting with DCM

ORD-Eintrag

ord-935f7472c4dc4879a30bc5496ba51ebc

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08778946B2