Multi-step reaction with 8 steps
1: 75 percent / Ph3P, diethyl azodicarboxylate / tetrahydrofuran
2: 1.) POCl3, 2.) aq. NaOH / 1.) 0 deg C, 30 min, 2.) RT, 1 h, 3.) reflux, 5 min
3: 54 percent / K2CO3 / dimethylformamide / 72 h
4: 84 percent / dioxane / 48 h / Heating
5: 53 percent / Et3N, trimethylsilyl trifluoromethanesulfonate / dioxane / 24 h / Ambient temperature
6: 59 percent / H2, 6 M aq. KOH / 10percent Pd/C / methanol; tetrahydrofuran / 3 h / 2585.7 Torr
7: 56 percent / ammonia (liq.), 4-(dimethylamino)pyridine / tetrahydrofuran / 24 h / 80 °C
8: 14 percent / Me2N(CH2)3N=C=NEt*HCl, DMAP / CH2Cl2
With
dmap; potassium hydroxide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; ammonia; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00091a010