Multi-step reaction with 14 steps
1.1: triethylamine; formic acid / palladium 10% on activated carbon / 120 h / 0 - 80 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
2.2: 3 h / 0 °C
3.1: bromine; pyridine / dichloromethane / 2 h / 0 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h
5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C
5.2: 12.25 h / 0 - 25 °C
6.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 12 h / 20 - 80 °C
7.1: 1,4-bis(9-O-dihydroquinidine)phthalazine; methanesulfonamide / water; tert-butyl alcohol / 12 h / 0 °C
7.2: 0.5 h / 25 °C
8.1: toluene-4-sulfonic acid / dichloromethane / 12 h / 25 °C
9.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C
9.2: 1 h / -78 °C
10.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C
11.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
11.2: 1.5 h / -78 °C
12.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 1 h / 100 °C / Microwave irradiation
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C
14.1: hydrogen / palladium 10% on activated carbon / methanol / 8 h / 50 °C / 37503.8 Torr
With
pyridine; formic acid; methanesulfonamide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; bromine; sodium hydride; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide;
bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;