Multi-step reaction with 13 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 23 °C
2.2: 0.5 h / 0 - 10 °C
3.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 22 °C
4.1: zinc / methanesulfonic acid / tetrahydrofuran / 5 h / Reflux
5.1: water; acetic acid / tetrahydrofuran / 10 h / 10 - 20 °C
6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 2 h / 20 °C
7.1: toluene / 0.25 h / 95 °C
8.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 1 h / -30 - -25 °C
9.1: hydrogenchloride / isopropyl alcohol; methanol / 1 h / 20 °C
10.1: pyridine / dichloromethane / 1 h / -10 - 0 °C
11.1: sodium iodide / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 22 °C
12.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
12.2: 1 h / 0 - 5 °C
13.1: sodium methylate; methanol / tetrahydrofuran / 1 h / 20 °C
With
pyridine; 1H-imidazole; chromium dichloride; hydrogenchloride; methanol; dmap; lithium borohydride; water; hydrogen; sodium methylate; potassium hexamethylsilazane; acetic acid; triethylamine; sodium iodide; nickel dichloride; zinc; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide;
methanesulfonic acid; palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
12.1: Nozaki-Hiyama-Kishi Coupling;