1: 2-(4-fluorophenyl)-5-[(1-methylethyl)oxy]-6-[(methylsulfonyl)amino]-1-benzofuran-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU in N,N-dimethyl-formamide T=21°C; 0.166667 h; 2: methylamine in tetrahydrofuran; N,N-dimethyl-formamide T=21°C; 18 h;

1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere 2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere 3.1: nitric acid / chloroform / 1 h / -15 - 0 °C 4.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 21 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 6.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 7.2: 18 h / 21 °C View Scheme

1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere 2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere 3.1: nitric acid / chloroform / 1 h / -15 - 0 °C 4.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 21 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 6.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 7.2: 18 h / 21 °C View Scheme

1.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere 2.1: nitric acid / chloroform / 1 h / -15 - 0 °C 3.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 21 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 5.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 6.2: 18 h / 21 °C View Scheme

1.1: nitric acid / chloroform / 1 h / -15 - 0 °C 2.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 21 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 5.2: 18 h / 21 °C View Scheme

1.1: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 21 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 4.2: 18 h / 21 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 2.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 3.2: 18 h / 21 °C View Scheme

1.1: sodium hydroxide; methanol / tetrahydrofuran / 16 h / 80 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h / 21 °C 2.2: 18 h / 21 °C View Scheme