Multi-step reaction with 10 steps
1: triethylamine / CH2Cl2 / 1 h / -5 °C
2: sodium iodide / acetone / 2 h / 50 °C
3: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min
4: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C
5: triethylamine / CH2Cl2 / 1 h / -5 °C
6: sodium iodide / acetone / 2 h / 50 °C
7: 1.) ethyl magnesium bromide, 2.) copper(I) bromide / 1.) THF, 2.) 50 deg C, 2 h
8: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C
9: 72 percent / pyridine-2,6-dicarboxylic acid, cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 - 2 °C
10: 1.) hydrogen, quinoline, 2.) 1M iron(III) chloride / 1.) Lindlar catalyst / 1.) ethyl acetate, room temperature, 2.) THF, room temperature, 30 min
With
quinoline; Pyridine-2,6-dicarboxylic acid; ammonium cerium(IV) nitrate; ethylmagnesium bromide; hydrogen; iron(III) chloride; toluene-4-sulfonic acid; sodium amide; triethylamine; sodium iodide; copper(I) bromide;
Lindlar's catalyst;
In
methanol; dichloromethane; water; acetone; acetonitrile;