hydrogenchloride; sodium nitrite 1. water, 0-5 deg C, 10 min; 2. water, acetone, room temperature, 48 h; Yield given. Multistep reaction;

1: Furane-3-carboxylic acid With HATU in N,N-dimethyl-formamide T=20°C; 0.25 h; 2: 3-iodo-4-methylphenylamine With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide T=20°C; 16 h;

PPA T=180°C; 1.5 h;

1: 1.) Li-Na alloy / 1.) ether, from -10 deg C to 10 deg C, 1.5 h, 2.) ether, from 0 deg C to RT, 3.5 h 2: 70 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 6 h / Heating 3: 25 percent / Li, NH3 / tetrahydrofuran / 0.25 h View Scheme

1: 83 percent / LiAlH4 / tetrahydrofuran / 22 h / Heating 2: 80 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 3: 92 percent / toluensulphonic acid / benzene / 4 h / Heating 4: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C -> -22 deg C, 2 h 5: 99 percent / pyridine / 40 h / 6 °C 6: chloramine-T / tetrahydrofuran / 1 h 7: 2,6-di-tert-butylpyridine, NaI / acetone / 17.5 h / 54 °C 8: 1.) LDA / 1.) DME, -78 deg C, 12 min, 2.) -78 deg C, 2 h 9: 1.) LDA / 1.) DME, -78 deg C, 10 min, 2.) -78 deg C -> 0 deg C, 25 min 10: 1.) m-CPBA, 2.) pyridine, 3.) Me2S, 4.) PhSH, NEt3 11: 88 percent / AcOH / tetrahydrofuran; H2O / 7 h / 21 °C View Scheme

Li (2percent Na); methyllithium 30-40 deg C, 3 h then 12 h, 20 deg C;