反应详情

温度

-78 °C

LiHMDS (1.0M in THF, 50 mL, 50 mmol) was added dropwise to a stirred solution of pyridin-3-ylamine (2.5 g, 26.4 mmol) in anhydrous THF (20 mL) under a nitrogen atmosphere at −70° C. After 10 min stirring at −78° C., a solution of 2,4-difluoro-1-nitrobenzene (4.0 g, 25.1 mmol) in THF (40 mL) was added dropwise at −78° C. The reaction mixture was slowly warmed to RT. After 4 h stirring at RT, the crude mixture was quenched by addition of an aqueous solution of NH4Cl and the aqueous fraction extracted with EtOAc. The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title compound as a red solid (quantitative). 1H NMR (CDCl3, 300 MHz): δ 9.58 (1H, br s), 8.61 (1H, d, J=2.64 Hz), 8.55 (1H, d, J=4.76 Hz), 8.29 (1H, dd, J=9.47, 5.92 Hz), 7.66-7.61 (1H, m), 7.40 (1H, dd, J=8.19, 4.75 Hz), 6.74 (1H, dd, J=10.95, 2.62 Hz), 6.60-6.51 (1H, m).

1. temperatureThe reaction mixture was slowly warmed to RT
2. stirringAfter 4 h stirring at RT
3. customthe crude mixture was quenched by addition of an aqueous solution of NH4Cl
4. extractionthe aqueous fraction extracted with EtOAc
5. washThe combined organic fractions were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo