Multi-step reaction with 9 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
2.1: Aliquat 336; sodium hypochlorite; ammonium chloride; ammonium hydroxide; sodium hydroxide / water; diethyl ether; tert-butyl methyl ether / 0 - 20 °C
3.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 0 - 20 °C
4.1: triethylamine; triphenylphosphine; bromine / dichloromethane / 2 h / 60 °C
5.1: ammonia / methanol / 32 h / 100 °C
6.1: trifluoroacetic acid / dichloromethane / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / tert-butyl alcohol / 12 h / 80 °C
8.1: hydrogen; palladium 10% on activated carbon / methanol / 1292.9 Torr
9.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h
9.2: 20 °C
With
ammonium hydroxide; sodium hypochlorite; palladium 10% on activated carbon; ammonia; hydrogen; bromine; Aliquat 336; ammonium chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide;
In
methanol; diethyl ether; dichloromethane; tert-butyl methyl ether; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/acs.jmedchem.8b00873