hydrogen; triethylamine; 5 palladium over charcoal in methanol T=0 - 20°C; 4 h;

hydrogen; ammonium formate; palladium on activated charcoal in ethanol T=50°C; 6 h;

1: 3-fluoro-5-iodo-2-(trimethylsilyl)pyridine; isopropylmagnesium chloride in tetrahydrofuran T=0°C; 0.0833333 h; 2: carbon dioxide in tetrahydrofuran 0.333333 h; 3: With sodium hydroxide in ethanol; water 0.0833333 h; Heating;

potassium permanganate in water 3 h; Heating;

1.1: BuLi; DABCO / hexane; diethyl ether / 1 h / -60 °C 1.2: 57 percent / diethyl ether; hexane / -60 °C 2.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 2.2: 78 percent / iodine / tetrahydrofuran; hexane 3.1: LDA / tetrahydrofuran; hexane / 2 h / -75 °C 3.2: H2O / tetrahydrofuran 4.1: tetrahydrofuran / 0.08 h / 0 °C 4.2: tetrahydrofuran / 0.33 h 4.3: 83 percent / NaOH / ethanol; H2O / 0.08 h / Heating View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 20 h / -75 °C 1.2: 87 percent / tetrahydrofuran; hexane 2.1: 88 percent / H2; ammonium formate / Pd/C / ethanol / 6 h / 50 °C View Scheme

1: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 2: 66 percent / potassium permanganate / H2O / 3 h / Heating View Scheme

1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight 2: thionyl chloride / Heating 3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 5: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 6: 66 percent / potassium permanganate / H2O / 3 h / Heating View Scheme

1: thionyl chloride / Heating 2: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 3: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 4: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 5: 66 percent / potassium permanganate / H2O / 3 h / Heating View Scheme

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating View Scheme