1: With Tl(OCOCF3)3 in trifluoroacetic acid T=20°C; 2 h; 2: With copper(ll) bromide in N,N-dimethyl-formamide T=120°C; 1 h;

1: 4-bromo-1H-indole-3-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane 1.5 h; Inert atmosphere; 2: methanol in dichloromethane T=0 - 20°C;

1: 86 percent / soddium chlorite, 2-methylbutene 2: diethyl ether View Scheme

manganese(IV) oxide; sodium cyanide T=20°C;

in diethyl ether Yield given;

1: 60.5 percent / 40percent NaOH / methanol / 1.5 h / Heating 2: 67.1 percent / phosphorus oxychloride/DMF / 1 h / Ambient temperature View Scheme

1.1: 69.1 percent / aq. NaOH / methanol / 1.5 h / Heating 2.1: KH; t-BuLi / diethyl ether; hexane / 0.33 h / -78 °C 2.2: B(n-BuO)3 / diethyl ether; hexane / -78 - 20 °C 2.3: 88 percent / aq. H3PO4 / diethyl ether; hexane / 0 - 20 °C View Scheme

1: 60.5 percent / 40percent NaOH / methanol / 1.5 h / Heating 2: 96.3 percent / H2O; acetic acid / 48 h / Ambient temperature 3: 89.1 percent / dimethylformamide; H2O / 1 h / Heating 4: 77.7 percent / 40percent aq. NaOH / methanol / 2 h / Heating View Scheme

sodium hydroxide in methanol 1.5 h; Heating;

1.1: 69.1 percent / aq. NaOH / methanol / 1.5 h / Heating 2.1: KH; t-BuLi / diethyl ether; hexane / 0.33 h / -78 °C 2.2: B(n-BuO)3 / diethyl ether; hexane / -78 - 20 °C 2.3: 88 percent / aq. H3PO4 / diethyl ether; hexane / 0 - 20 °C 3.1: Pd(PPh3)4 / toluene / 1 h / 20 °C 3.2: aq. Na2CO3 / toluene; ethanol / 8 h / 105 °C 3.3: 91 percent / HCl / diethyl ether / 20 °C View Scheme