Water → 3-(1-Isopropyl-1H-1,2,3-triazol-4-yl)-5-(4-morpholinophenyl)pyridin-2-amine

Temperature

100 °C

To a solution of 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine (100 mg, 0.35 mmol) and 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-morpholine (88 mg, 0.42 mmol) in 1,4-dioxane (7.0 mL)/water (3.0 mL) was added Cs2CO3 (227 mg, 0.70 mmol) at room temperature. The reaction mixture was purged with argon for 30 min. Then Pd(PPh3)4 (20.2 mg, 0.017 mmol) was added and allowed to stir at 100° C. for 16 h. The reaction mixture was cooled to RT, diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford crude compound. Crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 3-97% MeOH in DCM to afford the title compound as a yellow solid.

1. customThe reaction mixture was purged with argon for 30 min
2. temperatureThe reaction mixture was cooled to RT
3. washwashed with water (50 mL)
4. washThe organic layer was washed with brine solution (50 mL)
5. dry with materialdried over anhydrous Na2SO4 and solvent
6. customwas evaporated under reduced pressure
7. customto afford crude compound
8. customCrude compound was purified by column
9. washThe column was eluted with 3-97% MeOH in DCM

ORD record

ord-9a707cb815774d8f888ea2fe7d536108

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321748B2