反应详情

温度

-40 °C

5-(Hydroxymethyl)pyrimidine (16.2 g, 147 mmol) was dissolved in 500 mL of CH2Cl2 and cooled to −40° C. MsCl (16.0 g, 140 mmol) was added at 40° C. The mixture was stirred for 1 hour allowing to reach −20° C. The solution was used as such. 6-Nitroindole-1H-indole (35.6 g, 220 mmol) was dissolved in 750 mL of DMF and NaH (50%, 12 g, 250 mmol) was added in portions and the mixture was stirred for 1 hour. The mixture was cooled to −40° C. and the solution of the mesylate was added dropwise. The mixture was allowed to reach room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate (2×). The combined organic layers were washed with water (2×) and brine and dried over Na2SO4. After concentration in vacuo the material was purified by means of column chromatography (silica, heptane/ethyl acetate (1:1)→(1:4)) affording compound the title compound as a yellow solid (14 g, 55 mmol, 39%).

1. customto reach −20° C
2. stirringthe mixture was stirred for 1 hour
3. temperatureThe mixture was cooled to −40° C.
4. waitto reach room temperature overnight
5. customThe mixture was quenched with water
6. extractionextracted with ethyl acetate (2×)
7. washThe combined organic layers were washed with water (2×) and brine
8. dry with materialdried over Na2SO4
9. concentrationAfter concentration in vacuo the material
10. customwas purified by means of column chromatography (silica, heptane/ethyl acetate (1:1)→(1:4))