Multi-step reaction with 9 steps
1.1: sodium bistrimethylsilylamide / tetrahydrofuran / 0.5 h / -78 °C
1.2: 97 percent / tetrahydrofuran / -78 - 22 °C
2.1: 89 percent / LiCl; aq. Na2CO3; Pd2dba3 / various solvent(s) / 3 h / Heating
3.1: SmI2 / tetrahydrofuran / 0.75 h / -78 °C
3.2: 34 percent / MeOH / tetrahydrofuran / 2 h
4.1: 95 percent / H2O / dioxane / 24 h / Heating
5.1: (COCl)2; DMF / CH2Cl2 / 0.75 h / 22 °C
6.1: 960 mg / pyridine / CH2Cl2 / 1 h
7.1: 65 percent / tetrahydrofuran; diethyl ether / 4 h / 0 - 22 °C
8.1: 1-chloroethyl chloroformate / 2 h / 135 °C
8.2: 33 percent / MeOH / 1 h / Heating
9.1: 46 percent / KI; K2CO3 / acetonitrile / 20 h / Heating
With
pyridine; tris-(dibenzylideneacetone)dipalladium(0); samarium diiodide; oxalyl dichloride; carbonochloridic acid 1-chloro-ethyl ester; water; sodium hexamethyldisilazane; sodium carbonate; potassium carbonate; N,N-dimethyl-formamide; potassium iodide; lithium chloride;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; acetonitrile;
2.1: Suzuki coupling;
DOI:10.1021/jm0301484