Cesium carbonate → (3-Fluoro-[2,4]bipyridinyl-3'-yl)-methyl-amine

Temperature

100 °C

To a solution of compound (4-bromo-pyridin-3-yl)-methyl-amine (50 mg, 0.267 mmol, example 25, intermediate b) and 3-fluoro pyridine-2-boronic acid pinacol ester (Milestone Pharmtech LLC) (89.4 mg 0.4 mmol) dissolved in dry DMF (3 mL) in a sealed tube was added cesium carbonate (348.4 mg, 1.07 mmol) and the reaction mixture was purged with argon for 10 min. Then Pd(OAc)2 (9.38 mg, 0.013 mmol), dppf (1.48 mg, 0.0026 mmol) and CuCl (26.46 mg, 0.27 mmol) were added to the reaction mixture and again purged with nitrogen for 15 min. The reaction mixture was heated at 100° C. for 16 hours. The reaction mixture was cooled to 25° C., filtered through a bed of celite and washed with EtOAc. The organic layer was washed with water, dried over sodium sulphate and evaporated to yield the desired compound as a light yellow solid (50 mg, 92%) which was used in next step without further purification. MS (ESI): m/z=204.2 [M+H]+.

1. customthe reaction mixture was purged with argon for 10 min
2. customagain purged with nitrogen for 15 min
3. temperatureThe reaction mixture was cooled to 25° C.
4. filtrationfiltered through a bed of celite
5. washwashed with EtOAc
6. washThe organic layer was washed with water
7. dry with materialdried over sodium sulphate
8. customevaporated

ORD record

ord-14eb9e5da0274903844a74c9025557eb

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987307B2