Multi-step reaction with 10 steps
1.1: 91 percent / HNO3 / methanol / 0.25 h / -10 °C
2.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C
3.1: 5.47 g / pyridine / CH2Cl2 / 20 °C
4.1: 27 percent / trimethylacetic acid; K2CO3 / dimethylsulfoxide / 0.25 h / 80 °C
5.1: 68 percent / Et3N / CH2Cl2 / 20 °C
6.1: 78 percent / (Ph3P)4Pd; LiCl / dioxane / 85 °C
7.1: 91 percent / Fe; glacial AcOH / 80 °C
8.1: 80 percent / NaHB(OAc)3; AcOH / tetrahydrofuran; CH2Cl2 / 20 °C
9.1: 84 percent / aq. NaOH / methanol / 65 °C
10.1: 1-hydroxybenzotriazole; PS-carbodiimide / CH2Cl2; dimethylformamide / 0.25 h
10.2: 96 percent / N-methylmorpholine / CH2Cl2; dimethylformamide
With
pyridine; sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); PS-carbodiimide; oxalyl dichloride; nitric acid; sodium tris(acetoxy)borohydride; iron; potassium carbonate; benzotriazol-1-ol; acetic acid; triethylamine; N,N-dimethyl-formamide; lithium chloride; Trimethylacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
6.1: Stille coupling;
DOI:10.1021/jm030233b