反应详情

温度

90 °C

Dioxane (1.1 mL), phenylboronic acid (27 mg, 0.22 mmol), and potassium phosphate tribasic (70 mg, 0.33 mmol) were added to a nitrogen purged flask containing tert-butyl [(1S,2R)-2-({5-[(4-chloro-6-methylpyridin-2-yl)amino]-6-cyanopyridin-3-yl}amino)cyclohexyl]carbamate (PrepEx 1.7) (50 mg, 0.11 mmol). The flask was purged and flushed with nitrogen, and then PdCl2(dPPf)-CH2Cl2 (9 mg, 0.01 mmol) was added. The flask was purged with nitrogen, sealed, and heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with 10% aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (10 mL). The organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (10-50% ethyl acetate/hexanes, linear gradient) to afford tert-butyl (1S,2R)-2-(6-cyano-5-(6-methyl-4-phenylpyridin-2-ylamino)pyridin-3-ylamino)cyclohexylcarbamate. MS ESI calc'd. for C29H35N6O2 [M+H]+ 499. found 499.

1. customThe flask was purged
2. customflushed with nitrogen
3. customThe flask was purged with nitrogen
4. customsealed
5. temperatureThe reaction mixture was cooled to room temperature
6. additiondiluted with 10% aqueous sodium bicarbonate (10 mL)
7. extractionextracted with ethyl acetate (10 mL)
8. dry with materialThe organics were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by chromatography on silica gel (10-50% ethyl acetate/hexanes, linear gradient)