Dimethylformamide → HCID 71086712, compound

Temperature

45 °C

To a 100 mL round bottom flask that is adapted for magnetic stirring and equipped with a nitrogen inlet is charged (3-fluorophenyl)boronic acid (4.48 g, 32 mmol), 3,5-dichloro-2-cyanopyridine (5.8 g, 34 mmol), K2CO3 (5.5 g, 40 mmol), [1,1′-bis(diphenyphosphino)ferrocene]dichloro-palladium(II) [PdCl2(dppf)] (0.1 g, 0.13 mmol), dimethylformamide (50 mL) and water (5 mL). The reaction solution is agitated and heated to 45° C. and held at that temperature for 18 hours after which the completeness of the reaction can be determined by the absence of the starting material 3,5-dichloro-2-cyanopyridine via TLC using ethyl acetate/methanol (4:1) as the mobile phase and UV 435 nm to visualize any remaining starting material. The reaction solution is then cooled to room temperature and the contents partitioned between ethyl acetate (250 mL) and saturated aqueous NaCl (100 mL). The organic phase is isolated and washed a second time with saturated aqueous NaCl (100 mL). The organic phase is dried for 4 hours over MgSO4, the MgSO4 is removed by filtration and the solvent is removed under reduced pressure. The residue that remains is then slurried in methanol (50 mL) at room temperature for 20 hours. The resulting solid is collected by filtration and washed with cold methanol (50 mL) then hexanes (60 mL) and dried to afford desired product.

1. customTo a 100 mL round bottom flask that is adapted
2. customequipped with a nitrogen inlet
3. stirringThe reaction solution is agitated
4. customafter which the completeness of the reaction
5. temperatureThe reaction solution is then cooled to room temperature
6. customthe contents partitioned between ethyl acetate (250 mL) and saturated aqueous NaCl (100 mL)
7. customThe organic phase is isolated
8. washwashed a second time with saturated aqueous NaCl (100 mL)
9. dry with materialThe organic phase is dried for 4 hours over MgSO4
10. customthe MgSO4 is removed by filtration
11. customthe solvent is removed under reduced pressure
12. waitThe residue that remains is then slurried in methanol (50 mL) at room temperature for 20 hours
13. filtrationThe resulting solid is collected by filtration
14. washwashed with cold methanol (50 mL)
15. dry with materialhexanes (60 mL) and dried

ORD record

ord-0522ee41a79649c5bb119ad33f3ac33d

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865748B2