反应详情

A suspension of 4-bromo-2,5-dimethylaniline (4.00 g, 20 mmol), pyridin-3-ylboronic acid (2.70 g, 11 mmol), Pd2(dba)3 (0.55 g, 0.6 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.98 g, 1.2 mmol) and Na2CO3 (10.6 g, 100 mmol) in n-BuOH (50 mL) was degassed by a stream of argon gas for 15 min. The reaction flask was sealed and placed in a pre-heated oil bath (115° C.). After stirring overnight, the reaction was cooled and filtered. The filter cake was washed with DCM and the filtrate was concentrated in vacuo. The resulting residue was dissolved in EtOAc (150 mL). EtOAC was sequentially washed with water (20 mL), brine (20 mL), dried over Na2SO4 and evaporated. The crude product was purified by silica chromatography (0-50% EtOAC in hexanes gradient) to give 2,5-dimethyl-4-(pyridin-3-yl)aniline as a yellow solid; ESMS m/z 199.1 (M+H+).

1. customwas degassed by a stream of argon gas for 15 min
2. customThe reaction flask was sealed
3. customplaced in a pre-heated oil bath
4. custom(115° C.)
5. temperaturethe reaction was cooled
6. filtrationfiltered
7. washThe filter cake was washed with DCM
8. concentrationthe filtrate was concentrated in vacuo
9. dissolutionThe resulting residue was dissolved in EtOAc (150 mL)
10. washEtOAC was sequentially washed with water (20 mL), brine (20 mL)
11. dry with materialdried over Na2SO4
12. customevaporated
13. customThe crude product was purified by silica chromatography (0-50% EtOAC in hexanes gradient)