Multi-step reaction with 12 steps
1.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate / 1,4-dioxane; butan-1-ol / 1 h / 100 °C / Inert atmosphere
2.1: sodium methylate; methanol / 1.5 h
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
3.2: -78 - 20 °C
4.1: titanium(IV) tetraethanolate / dichloromethane / 24 h / 20 °C
5.1: 1-methyl-pyrrolidin-2-one; diethyl ether / 6.17 h / -8.5 - 5 °C
6.1: hydrogenchloride / 1,4-dioxane; methanol / 0.25 h / 20 °C
7.1: isopropylmagnesium bromide / tetrahydrofuran; 2-methyltetrahydrofuran / -20 - 20 °C
8.1: phosphorus pentachloride / dichloromethane / 1.5 h / 20 °C
9.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water / 95 °C
10.1: trifluoroacetic acid / chloroform / 36 °C
11.1: triethylamine; diphenyl phosphoryl azide / toluene / 0.5 h / 80 - 90 °C
12.1: sodium hydroxide / 1,4-dioxane; water / 1 h / 90 °C
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; methanol; titanium(IV) tetraethanolate; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); oxalyl dichloride; phosphorus pentachloride; diphenyl phosphoryl azide; isopropylmagnesium bromide; sodium methylate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; dichloromethane; chloroform; water; toluene; butan-1-ol;
1.1: |Suzuki Coupling / 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 9.1: |Suzuki Coupling;
DOI:10.1021/ml4001485