Multi-step reaction with 16 steps
1.1: potassium iodate; iodine / water; acetic acid / 20 h / 20 °C
2.1: potassium carbonate / acetonitrile / 2 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere
3.2: 0.58 h / -78 °C
4.1: methanesulfonic acid / methanol / 14.5 h / 20 °C
5.1: pyridine; acetic anhydride / dmap / 19 h / 4 - 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / 1.5 h / 4 °C / Inert atmosphere
7.1: hydrogen / palladium on activated charcoal / methanol / 2 h / 20 °C
8.1: bromine / acetic acid / 20 °C
9.1: water; triethylamine / methanol / 25 h / 20 - 50 °C
10.1: chloro-trimethyl-silane; triethylamine / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere
11.2: 1 h / -78 °C
12.1: methanesulfonic acid / methanol / 0.5 h / 20 °C
13.1: pyridine; acetic anhydride / dmap / 30 h / 20 °C
14.1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / 0.5 h / 4 - 20 °C / Inert atmosphere
15.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 0.33 h / 120 °C / Microwave irradiation; Inert atmosphere
16.1: 1,1'-carbonyldiimidazole / chloroform / 1 h / 20 °C
16.2: 18 h / 20 °C
With
pyridine; triethylsilane; n-butyllithium; chloro-trimethyl-silane; methanesulfonic acid; potassium iodate; boron trifluoride diethyl etherate; water; hydrogen; bromine; iodine; acetic anhydride; potassium carbonate; triethylamine; 1,1'-carbonyldiimidazole;
dmap; palladium on activated charcoal; palladium diacetate; tris-(o-tolyl)phosphine;
In
tetrahydrofuran; methanol; hexane; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
15.1: Heck Reaction;