Multi-step reaction with 8 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
2: Aliquat 336; sodium hypochlorite; ammonium chloride; ammonium hydroxide; sodium hydroxide / water; diethyl ether; tert-butyl methyl ether / 0 - 20 °C
3: 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: triethylamine; triphenylphosphine; bromine / dichloromethane / 2 h / 60 °C
5: ammonia / methanol / 32 h / 100 °C
6: trifluoroacetic acid / dichloromethane / 20 °C
7: N-ethyl-N,N-diisopropylamine; cesium fluoride / tert-butyl alcohol / 96 h / 95 °C / Sealed tube
8: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,2-dimethoxyethane / 18 h / 80 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; sodium hypochlorite; ammonia; bromine; Aliquat 336; sodium carbonate; ammonium chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; sodium hydroxide;
In
methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; tert-butyl methyl ether; water; ethyl acetate; tert-butyl alcohol;
8: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.8b00873