Multi-step reaction with 14 steps
1.1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C
2.1: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C
3.1: 94 percent / AcOH; conc. HCl / 24 h / 118 °C
4.1: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C
5.1: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C
6.1: 69 percent / Na / methanol / 2 h / 20 °C
7.1: 87 percent / dimethylformamide / 2.25 h / 85 °C
8.1: 40 percent / NBS; dibenzoyl peroxide / CCl4 / 3.5 h / 120 °C / Irradiation
9.1: 48 percent / 2,6-lutidine / dimethylformamide / 16 h / 120 °C
10.1: 70 percent / aq. NaOH / tetrahydrofuran / 2 h / 20 °C
11.1: 73 percent / Et3N / dimethylformamide / 0.75 h / 20 °C
12.1: 91 percent / dimethylformamide / 2.5 h / 20 °C
13.1: NaH / dimethylformamide / 0.05 h / 20 °C
13.2: 62 percent / dimethylformamide / 3 h / 20 °C
14.1: TFA / CH2Cl2 / 20 °C
With
pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; dihydrogen peroxide; bromine; sodium; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; dibenzoyl peroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm011081s