Sodium Hydroxide → HCID 67119555, compound

To a solution of ethyl ethynyl ether (3.6 g, 25.7 mmol) in tetrahydrofuran (10 mL) was added catechol borane (3.08 g, 25.7 mmol) on an ice bath. Immediately, the cold bath was removed, the reaction mixture was allowed to room temperature, and then, the solution was stirred for 1.5 hours under reflux. This reaction mixture was allowed to room temperature. To this mixture solution were added 2-amino-6-chloro-nicotinic acid methyl ester (1.6 g, 8.57 mmol), sodium hydroxide powder (1.13 g, 28.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.99 g, 0.857 mmol) and dioxane (20 mL), which was then stirred for 2 hours under reflux. The reaction mixture was allowed to room temperature, and partitioned into water and ethyl acetate. The organic layer was separated, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography, and the title compound (1.30 g, 5.85 mmol, 68%) was obtained as a brown solid.

1. customImmediately, the cold bath was removed
2. customwas allowed to room temperature
3. temperatureunder reflux
4. customwas allowed to room temperature
5. stirringwas then stirred for 2 hours
6. temperatureunder reflux
7. customwas allowed to room temperature
8. custompartitioned into water and ethyl acetate
9. customThe organic layer was separated
10. customthe solvent was evaporated in vacuo
11. customthe residue was purified by silica gel column chromatography

ORD record

ord-aa04f6188f2f43e58754724e029dda48

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932272B2