Multi-step reaction with 14 steps
1.1: 50 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethyl acetate / 5 h / Heating
2.1: trifluoroacetic acid / H2O / 1 h / 25 °C
2.2: 85 percent / HATU; i-Pr2NEt / CH2Cl2 / 3 h / 25 °C
3.1: 82 percent / imidazole / dimethylformamide / 16 h / 25 °C
4.1: 80 percent / Lawesson reagent / benzene / 16 h / Heating
5.1: 92 percent / HF*pyridine; pyridine / tetrahydrofuran / 2 h / 25 °C
6.1: N,N-diethylaminosulfur trifluoride / CH2Cl2 / 1 h / -78 °C
7.1: BrCCl3; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 1 h / 0 °C
8.1: trifluoroacetic acid / CH2Cl2 / 1 h / 25 °C
9.1: HATU; i-Pr2NEt / CH2Cl2 / 24 h / 25 °C
10.1: Me3SnOH / 1,2-dichloro-ethane / 5 h / 80 °C
11.1: HATU; i-Pr2NEt / CH2Cl2 / 16 h / 25 °C
12.1: 85 percent / N,N-diethylaminosulfur trifluoride / CH2Cl2 / 1 h / -25 °C
13.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 25 °C
With
Lawessons reagent; pyridine; 1H-imidazole; Bromotrichloromethane; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trimethyltin(IV) hydroxide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;
DOI:10.1002/anie.200602798