Potassium Phosphate, Tribasic → 2-(5-(6-Fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

Temperature

100 °C

To a solution of the title compound from Example 2 Step D (0.1855 g, 0.704 mmol) and the title compound from Example 2 Step B (0.10 g, 0.586 mmol) in tetrahydrofuran (5.86 mL) were added palladium acetate (0.013 g, 0.059 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.048 g, 0.117 mmol), and potassium phosphate tribasic (0.373 g, 1.759 mmol). The resulting mixture was heated at 100° C. for 18 hours. The mixture was then cooled to room temperature, filtered with the aid of ethyl acetate, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (30-50% acetone in dichloromethane) provided the title compound: LCMS m/z 273.99 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.99 (d, J=1.6 Hz, 1H), 8.72 (d, J=2.2 Hz, 1H), 8.39 (t, J=2.0 Hz, 1H), 8.10 (t, J=2.6 Hz, 1H), 7.96 (s, 1H), 7.63 (dd, J=9.9, 4.8 Hz, 1H), 7.17-7.13 (m, 1H), 2.00 (br s, 1H), 1.68 (s, 6H).

1. temperatureThe mixture was then cooled to room temperature
2. filtrationfiltered with the aid of ethyl acetate
3. concentrationconcentrated under reduced pressure
4. customPurification by flash chromatography on silica gel (30-50% acetone in dichloromethane)

ORD record

ord-9a82523955cc4824a5c773e7828d0fc3

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09173873B2