反应详情

温度

110 °C

1-Benzyl-5-chloro-2-(1,3-thiazol-2-yl)-1H-pyrrolo[3,2-b]pyridine (30 mg, 0.092 mmol, from Step 1), di-tert-butyl hydrazine-1,2-dicarboxylate (26 mg, 0.11 mmol) and Cs2CO3 (30 mg, 0.092 mmol) were combined in toluene (2.8 mL) and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (7.2 mg, 0.0092 mmol) was added. The mixture was degassed by a stream of nitrogen through the solution for 10 minutes. The reaction was heated to 110° C. overnight. The intermediate di-tert-butyl 1-[1-benzyl-2-(1,3-thiazol-2-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH) and was isolated in the amount of 20 mg after evaporation of eluent. The resulting residue was dissolved in acetic acid (1.9 mL) and heated in the microwave to a temperature of 165° C. for 5 minutes. AcOH was removed in vacuo and the residue was reconstituted and purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (4.6 mg, 14%).

1. customThe mixture was degassed by a stream of nitrogen through the solution for 10 minutes
2. customThe intermediate di-tert-butyl 1-[1-benzyl-2-(1,3-thiazol-2-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate was purified via preparative HPLC-MS (C18
3. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH) and
4. customwas isolated in the amount of 20 mg
5. customafter evaporation of eluent
6. dissolutionThe resulting residue was dissolved in acetic acid (1.9 mL)
7. temperatureheated in the microwave to a temperature of 165° C. for 5 minutes
8. customAcOH was removed in vacuo
9. custompurified via preparative HPLC-MS (C18
10. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)