Multi-step reaction with 13 steps
1.1: Br2; NaOAc / acetic acid / Heating
2.1: benzene / 4.5 h
3.1: 4.19 g / NaOH / CHCl3; H2O / 1.5 h / cooling
4.1: toluene / 108 h / Heating
4.2: 87 percent / NaOMe / methanol / 1 h
5.1: 67 percent / NaI; TBDMSCl / acetonitrile / 48 h / 20 °C
6.1: 80 percent / NH4F / methanol / 18 h / Heating
7.1: NH3 / methanol / 43 h / 90 °C
8.1: 1.42 g / imidazole / dimethylformamide / 24 h
9.1: 72 percent / PyBOP; diisopropylethylamine / CH2Cl2 / 6 h / 20 °C
10.1: H2 / 10 percent Pd/C / methanol; tetrahydrofuran / 1 h
11.1: 0.37 g / pyridine / tetrahydrofuran / 1.25 h / 0 °C
12.1: 84 percent / Et3N*3HF / tetrahydrofuran / 24 h
13.1: 93 mg / DMAP / pyridine
With
pyridine; 1H-imidazole; dmap; ammonium fluoride; sodium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia; hydrogen; bromine; sodium acetate; tert-butyldimethylsilyl chloride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1021/tx025588x