反应详情

温度

-78 °C

A solution of LDA (1.8 M in THF/heptane/ethyl benzene, 340 mL, 0.6 mmol) was added slowly to a stirred solution of isobutyl-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-trifluoromethyl-phenyl)-amine (135 g, 0.3 mmol) under N2 at −78° C. After 30 minutes dimethyl carbonate (55 mg, 0.6 mmol) was added. After stirring at −78° C. for 30 minutes, the solution was allowed to warm up slowly and stirred at 0° C. for 30 minutes. The reaction was quenched with saturated aqueous NH4Cl (1 mL). The mixture was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 (2×). The combined extracts were washed with brine, then dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography on silica gel (40-80% CH2Cl2 in heptane) to give the product as light yellow oil (75 mg, 49%). 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=7.91 Hz, 2H), 7.70 (d, J=8.29 Hz, 2H), 7.65 (d, J=8.29 Hz, 2H), 7.40 (d, J=8.29 Hz, 2H), 7.14 (s, 1H), 6.50 (s, 1H), 3.96 (d, J=7.16 Hz, 2H), 3.69 (s, 3H), 3.51 (s, 2H), 2.05-2.22 (m, 1H), 0.98 (d, J=6.78 Hz, 6H). MS m/e 511.2 (M+H).

1. temperatureto warm up slowly
2. stirringstirred at 0° C. for 30 minutes
3. customThe reaction was quenched with saturated aqueous NH4Cl (1 mL)
4. customThe mixture was partitioned between CH2Cl2 and H2O
5. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
6. washThe combined extracts were washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. customevaporated
10. customThe residue was purified by column chromatography on silica gel (40-80% CH2Cl2 in heptane)