Multi-step reaction with 11 steps
1.1: potassium carbonate / acetonitrile / 0.5 h
1.2: 20 °C
2.1: hydrogen; methyl 2-(4-chlorophenyl)-2-(4-nitro-2H-indazol-2-yl)acetate / 10% Pt/activated carbon / 48 h / 20 °C
3.1: sodium carbonate / 1,4-dioxane; water / 48 h / 0 - 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
5.1: hydrogenchloride; methanol / 2 h / 20 °C
5.2: pH 9 - 10
6.1: 4-methyl-morpholine / dichloromethane / 20 °C
7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
7.2: 2 h / 20 °C
8.1: lithium borohydride; methanol / tetrahydrofuran / 2 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 °C
10.1: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 20 °C
11.1: sodium hydride / dimethyl sulfoxide; mineral oil / 3 h / 20 °C
11.2: 16 h / 70 °C
With
4-methyl-morpholine; hydrogenchloride; methanol; lithium borohydride; methyl 2-(4-chlorophenyl)-2-(4-nitro-2H-indazol-2-yl)acetate; hydrogen; sodium hydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride;
10% Pt/activated carbon;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil;