Multi-step reaction with 10 steps
1: 10percent aq. Na2CO3 / CH2Cl2 / 0.5 h / 0 °C
2: liquid ammonia / CH2Cl2 / 16 h / Heating
3: HOAc / ethanol / 0.5 h / Heating
4: 80 percent / P2S5, NaHCO3 / bis-(2-methoxy-ethyl) ether / 3 h / 80 - 85 °C
5: 83 percent / hydrazine / propan-2-ol; tetrahydrofuran / 0.25 h / Ambient temperature
6: 92 percent / silica gel / toluene / 3 h / Heating
7: 1.) t-BuOK, triethyl phosphite, 2.) O2 / 1.) THF, t-BuOH, DMF, from -20 to -10 deg C, 1 h
8: SOCl2 / CH2Cl2 / 2 h / Ambient temperature
9: Et3N / 0.08 h / Heating
10: 51 percent / PPh3, CuI, Et3N, palladium acetate / dimethylformamide / 72 h / Ambient temperature
With
copper(l) iodide; thionyl chloride; tetraphosphorus decasulfide; potassium tert-butylate; ammonia; oxygen; palladium diacetate; silica gel; sodium hydrogencarbonate; sodium carbonate; acetic acid; triethylamine; triphenylphosphine; hydrazine; triethyl phosphite;
In
tetrahydrofuran; ethanol; dichloromethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1021/jm00107a048