Multi-step reaction with 11 steps
1.1: 77 percent / N,N-diisopropylethylamine / acetonitrile / 6 h / 90 °C
2.1: H2 / 5percent Pt/C / tetrahydrofuran / 6 h
3.1: N,N-dimethylaniline / tetrahydrofuran / 17 h / 20 °C
4.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C
4.2: 77 percent / tetrahydrofuran / 24 h / -78 - 20 °C
5.1: NEt3 / CH2Cl2 / 0.75 h / 0 °C
6.1: acetonitrile / 48 h / 95 °C
7.1: 99 percent / hydrazine monohydrate / methanol / 5 h / 80 °C
8.1: 89 percent / pyridine / 18 h / 0 - 20 °C
9.1: 77 percent / H2 / 10percent Pd/C / ethanol / 23 h
10.1: 82 percent / ethanol; tetrahydrofuran / Heating
11.1: 89 percent / NaOH / ethanol / 20 °C
With
pyridine; sodium hydroxide; hydrogen; hydrazine hydrate; N,N-dimethyl-aniline; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;
5percent Pt/C; 10percent Pd/C;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;
1.1: Substitution / 2.1: Reduction / 3.1: Acylation / 4.1: Metallation / 4.2: Ring cleavage / 5.1: mesylation / 6.1: Substitution / 7.1: hydrazinolysis / 8.1: Acetylation / 9.1: Hydrogenolysis / 10.1: Condensation / 11.1: Ring cleavage;
DOI:10.1021/jm990373e