Multi-step reaction with 12 steps
1.1: 91 percent / K2CO3 / dimethylformamide / 2 h / 90 °C
2.1: dimethylformamide / 24 h / Heating
2.2: 82 percent / aq. HCl / diethyl ether / 2 h / Heating
3.1: 93 percent / trifluoroacetic acid / 24 h / 20 °C
4.1: 92 percent / Amberlyst H-15 / CH2Cl2 / 16 h / 20 °C
5.1: 98 percent / K2CO3 / dimethylformamide / 2 h / 90 °C
6.1: 98 percent / Amberlyst H-15 / tetrahydrofuran / 24 h / 20 °C
7.1: 89 percent / NaBH4; iodine / tetrahydrofuran / 4 h / Heating
8.1: 93 percent / Et3N / CH2Cl2 / 2 h / 20 °C
9.1: 89 percent / NaBH4 / copper acetylacetonate / CH2Cl2; propan-2-ol; methanol / 0.5 h / Heating
10.1: 90 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 16 h / 20 °C
11.1: 1-hydroxybenzotriazole; diisopropylcarbodiimide / dimethylformamide / 0.25 h / 20 °C
11.2: dimethylformamide / 2 h / 20 °C
12.1: 84 percent / Cs2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 0.5 h / 80 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; Amberlyst H-15; iodine; potassium carbonate; benzotriazol-1-ol; caesium carbonate; triethylamine; trifluoroacetic acid; diisopropyl-carbodiimide;
copper acetylacetonate; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
12.1: Suzuki coupling;
DOI:10.1039/b400110a