Multi-step reaction with 10 steps
1.1: pyridine; dmap / 24 h / Inert atmosphere
2.1: morpholine / dichloromethane / 2 h / Inert atmosphere; Reflux
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere
4.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / Inert atmosphere
5.1: methanol; sodium methylate / 6 h / Inert atmosphere
6.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere
6.2: Inert atmosphere
7.1: pyridine; dmap / N,N-dimethyl-formamide / Inert atmosphere
8.1: acetic acid / water / 3 h / Reflux; Inert atmosphere
9.1: pyridine; dmap / 60 °C / Inert atmosphere
10.1: methanol; toluene-4-sulfonic acid / dichloromethane / Inert atmosphere
With
morpholine; pyridine; methanol; dmap; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2012.04.035