Cesium carbonate → HCID 66721782, compound

Temperature

98 °C

To a mixture of potassium cyclopropyltrifluoroborate (0.943 g, 6.37 mmol), palladium (II) acetate (0.0285 g, 0.126 mmol), di-1-adamantylbutylphosphine [CAS 321921-71-5] (0.0678 g, 0.189 mmol) and Cs2CO3 (6.165 g, 18.922 mmol) in toluene (20 ml) and water (4 ml) under a nitrogen atmosphere was added 2-chloro-4-nitropyridine (1 g, 6.307 mmo). The reaction mixture was heated at 98° C. for 2 days. After cooling, the mixture was washed with water. The organic phase was separated and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel; Heptane/DCM from 100/0 to 50/50 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D52 (0.800 g, 77%) as yellow oil which crystallized upon standing

1. temperatureAfter cooling
2. washthe mixture was washed with water
3. customThe organic phase was separated
4. dry with materialdried (Na2SO4)
5. concentrationThe filtrate was concentrated in vacuo
6. customthe residue was purified by column chromatography (silica gel; Heptane/DCM from 100/0 to 50/50 as eluent)
7. customThe desired fractions were collected
8. concentrationconcentrated in vacuo
9. customto yield intermediate compound D52 (0.800 g, 77%) as yellow oil which
10. customcrystallized

ORD record

ord-fe296db1cd0946a793a0fb80b1013e09

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716480B2