Multi-step reaction with 12 steps
1: 97 percent / potassium hydride, 1,3-diaminopropane / 18 h / Ambient temperature
2: 93 percent / imidazole, / dimethylformamide / 2 h / Ambient temperature
3: 93 percent / Et3N, CuI / (Ph3P)2PdCl2 / 4 h / 50 °C
4: 93 percent / H2 / 5percent Pd-C / ethanol; ethyl acetate / 4 h
5: 1 M tetrabutylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature
6: 90 percent / triphenylphosphine, imidazole, I2 / toluene / 0.5 h / 65 °C
7: K2CO3 / dimethylformamide / 1.5 h / 90 °C
8: toluene / 1 h / 50 °C
9: 50percent m-chloroperoxybenzoic acid / CH2Cl2 / 15 h / Ambient temperature
10: trifluoroacetic anhydride / dimethylformamide / 18 h / Ambient temperature
11: SOCl2 / toluene / 4 h / Ambient temperature
12: Cs2CO3 / dimethylformamide / 1.5 h / 60 °C
With
1H-imidazole; copper(l) iodide; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hydride; potassium carbonate; caesium carbonate; Trimethylenediamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride;
bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00046a017