Multi-step reaction with 10 steps
1.1: 84 percent / AcOH; KOAc / 1.5 h / 20 °C
2.1: Fe; aq. HOAc / ethanol / 0.5 h / Heating
3.1: ethanol / 3 h / Heating
4.1: 54 percent / 50percent aq. HBF4; NaNO2 / -20 - -10 °C
5.1: POCl3 / 1.83 h / Heating
6.1: aq. HCl / propan-2-ol / 0.5 h / 60 °C
7.1: tributyltin hydride; AIBN / 16 h / 90 °C
7.2: tetrakistriphenylphosphinepalladium(0) / dimethylformamide / 1.25 h / 100 °C
8.1: 94 percent / H2 / PtO2*xH2O / methanol; tetrahydrofuran / 18 h / 3102.97 Torr
9.1: 91 percent / NH3 / propan-2-ol / 20 h / 100 °C
10.1: 8 percent / 1-hydroxybenzotriazole; Et3N; EDCI*HCl / tetrahydrofuran; N,N-dimethyl-acetamide / 1008000 h / 20 °C
With
hydrogenchloride; 2,2'-azobis(isobutyronitrile); ammonia; hydrogen; tri-n-butyl-tin hydride; potassium acetate; iron; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium nitrite; trichlorophosphate;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; N,N-dimethyl acetamide; isopropyl alcohol;
1.1: Bromination / 2.1: Reduction / 3.1: cyclocondensation / 4.1: Fluorination / 5.1: Chlorination / 6.1: Condensation / 7.1: stannylation / 7.2: alkenylation / 8.1: Catalytic hydrogenation / 9.1: Substitution / 10.1: Acylation;
DOI:10.1021/jm990482t