Multi-step reaction with 17 steps
1.1: toluene-4-sulfonic acid / benzene / Reflux
2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 °C
3.1: tetrahydrofuran / 20 °C / Inert atmosphere; Sealed tube
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere; Sealed tube
5.1: 3 h / 100 °C / Neat (no solvent)
6.1: trichlorophosphate; N,N-dimethyl-aniline / 18 h / 20 °C
6.2: 0 °C
7.1: ammonia / methanol / 18 h / 100 °C / Sealed tube
8.1: hydrogenchloride; water / 1,4-dioxane; ethanol / 80 °C / Sealed tube
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 50 °C
10.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C
10.2: 18 h / 20 °C
11.1: hydrogen / 5% Pd(II)/C(eggshell) / ethyl acetate / 18 h / Inert atmosphere; Sealed tube
12.1: N-iodo-succinimide / acetonitrile / 18 h / 20 °C
13.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 18 h / 100 °C / Inert atmosphere; Sealed tube
14.1: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.5 h / 150 °C / Inert atmosphere; Sealed tube; Microwave irradiation
15.1: N-Bromosuccinimide / acetonitrile / 18 h / 20 °C
16.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 100 °C
17.1: trifluoroacetic acid; water
With
hydrogenchloride; potassium phosphate; N-Bromosuccinimide; N-iodo-succinimide; lithium hydroxide monohydrate; ammonia; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; trichlorophosphate;
tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 5% Pd(II)/C(eggshell);
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; acetonitrile; mineral oil; benzene;
16.1: Stille Coupling;