Реакция #360685

Уравнение реакции

7-(2-chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-ylamine

1-[2-(4-bromophenoxy)-ethyl] pyrrolidine

Cs2CO3

Xantphos

→

[7-(2 chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Растворители

dioxane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was cooled to room temperature
2. 2
   Фильтрацияfiltered
3. 3
   workup.DISSOLUTIONThe filtrate was dissolved in EtOAc
4. 4
   Промывкаwashed with saturated NaHCO3 and brine and organic phase
5. 5
   Сушкаwas dried (Na2SO4)
6. 6
   КонцентрированиеThe organics were concentrated under reduced pressure
7. 7
   Другоеto afford residue
8. 8
   Другоеthat was precipitated out

Методика

7-(2-chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-ylamine (0.67 mmol, 1.0 equiv), 1-[2-(4-bromophenoxy)-ethyl] pyrrolidine (0.005 mmol, 1.5 equiv), Cs2CO3 (2.01 mmol, 3.0 equiv), Pd2(dba)3 (0.067 mmol, 0.1 equiv), and Xantphos (0.134 mmol, 0.2 equiv) were dissolved in 20 mL dioxane, placed under an argon atmosphere and refluxed at 100° C. for 18 h. The reaction was cooled to room temperature and filtered. The filtrate was dissolved in EtOAc, washed with saturated NaHCO3 and brine and organic phase was dried (Na2SO4). The organics were concentrated under reduced pressure to afford residue that was precipitated out using EtOAc/hexanes (1:5 v/v) to give [7-(2 chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine, as an orange solid (271.2 mg, 83% yield). Rf=0.56 (9:1 DCM/MeOH). MS (ES+) m/z=491. LC retention time 2.72 min.

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