Multi-step reaction with 10 steps
1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere
2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere
3.1: nitric acid / chloroform / 1 h / -15 - 0 °C
4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 21 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C
7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C
7.2: 18 h / 21 °C
8.1: potassium carbonate / acetonitrile / 24 h / 65 °C / Inert atmosphere
9.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 760.05 Torr
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C
With
methanol; hydrogen; nitric acid; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; zinc(II) chloride;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;