反应详情

温度

90 °C

To a 50 mL pear flask were added (S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (153 mg, 0.602 mmol) and tert-butyl 1,4-diazepane-1-carboxylate (241 mg, 1.20 mmol). After evacuating the flask and flushing it with nitrogen, the flask was charged with dioxane (1.6 mL) and potassium 2-methylpropan-2-olate (1.0 M in THF) (1.32 mL, 1.32 mmol). The mixture was then heated to 90° C. for 1 hour. After cooling, the mixture was worked up with saturated NaHCO3 and EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC (acid mode, 25-50% ACN/water gradient). The product-containing fractions were combined, neutralized with saturated NaHCO3, concentrated in vacuo to remove ACN, and then extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (76 mg, 34%). ESI-MS m/z [M+H]+ calc'd for C20H31N5O2, 374. found 374.

1. customAfter evacuating the flask
2. customflushing it with nitrogen
3. temperatureAfter cooling
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by preparative HPLC (acid mode, 25-50% ACN/water gradient)
8. concentrationconcentrated in vacuo
9. customto remove ACN
10. extractionextracted with EtOAc
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo