Multi-step reaction with 12 steps
1.1: lithium tetrafluoroborate / ethylene glycol / 3.5 h / 95 °C / Inert atmosphere
2.1: potassium phosphate monohydrate / palladium diacetate; di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine / toluene / 6 h / 90 - 100 °C / Inert atmosphere
3.1: sodium hydroxide; water / tetrahydrofuran / 20 °C / Inert atmosphere
3.2: pH 5 - 6
4.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: methoxycarbonylsulfamoyl-triethylammmonium hydroxide / tetrahydrofuran / 1.42 h / 0 °C / Inert atmosphere; Reflux
6.1: copper(ll) bromide; hexamethylenetetramine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride; water / tetrahydrofuran / 20 °C / Inert atmosphere
8.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
9.1: oxalyl dichloride / N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere
10.1: sodium azide / water; acetone / 1 h / 0 °C / Inert atmosphere
11.1: xylene / 0.08 h / 140 °C / Inert atmosphere
11.2: 0.08 h / 140 °C / Inert atmosphere
12.1: sodium hydride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere
12.2: 0.58 h / 0 - 20 °C / Inert atmosphere
With
hydrogenchloride; dmap; lithium tetrafluoroborate; sodium azide; potassium phosphate monohydrate; methoxycarbonylsulfamoyl-triethylammmonium hydroxide; oxalyl dichloride; hexamethylenetetramine; water; sodium hydride; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; copper(ll) bromide;
palladium diacetate; N,N-dimethyl-formamide; di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine;
In
tetrahydrofuran; dichloromethane; water; ethylene glycol; acetone; toluene; xylene;
11.1: Curtius Rearrangement;