Potassium Phosphate, Tribasic → 3-(2-fluoro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

温度

80 °C

3-Bromo-5-nitro-1-trityl-1H-indazole 3BI (15.64 g, 32.3 mmol), 2-fluoro-4-pyridine boronic acid 2BV (5.0 g, 35.5 mmol), K3PO4 (17.1 g, 80.7 mmol) and Pd(dppf)Cl2 (2.64 g, 3.23 mmol) was mixed in dioxane/H2O (240 mL/60 mL) at rt and heated at 80° C. overnight. The reaction mixture was cooled to rt and concentrated to a small volume. The residue was partitioned between ethyl acetate (200 mL) and brine (150 mL). The organic layer was washed with brine, dried (MgSO4) and filtered. The resulting filtrate was concentrated and the residue was purified on silica gel column eluting with hexanes, 5% ethyl acetate in hexanes, 10% ethyl acetate in hexanes sequentially to yield a yellow solid 3BV (3.33 g, 64%).

1. temperatureThe reaction mixture was cooled to rt
2. concentrationconcentrated to a small volume
3. customThe residue was partitioned between ethyl acetate (200 mL) and brine (150 mL)
4. washThe organic layer was washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationThe resulting filtrate was concentrated
8. customthe residue was purified on silica gel column
9. washeluting with hexanes, 5% ethyl acetate in hexanes, 10% ethyl acetate in hexanes sequentially
10. customto yield a yellow solid 3BV (3.33 g, 64%)

ORDレコード

ord-542fcdd65bef4bacbc658574ac44e3ac

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08716483B2