Multi-step reaction with 10 steps
1.1: N,N-dimethyl-formamide / 20 °C
2.1: boron tribromide / dichloromethane / 20 °C
2.2: 20 °C
3.1: sodium t-butanolate / tetrahydrofuran / 0.25 h / 0 - 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
4.2: 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 60 °C
5.2: 0 °C
6.1: sodium dithionite / tetrahydrofuran; water / 1 h / 20 °C
7.1: tert.-butylnitrite; copper dichloride / acetonitrile / 0.25 h / 50 °C
8.1: hydrazine / ethanol / 8 h / Reflux
9.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 0.75 h / 20 °C
9.2: 20 °C
10.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.17 h / 135 °C / Microwave
With
tert.-butylnitrite; sodium dithionite; boron tribromide; sodium hydride; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; copper dichloride; sodium t-butanolate; hydrazine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;