in tetrahydrofuran; methanol

1: formic acid With acetic anhydride T=0 - 50°C; Inert atmosphere; 2: 2-fluoro-phenylamine in tetrahydrofuran T=20°C; Inert atmosphere; 3: With hydrogenchloride; borane-THF

1: 2-fluoro-phenylamine With n-butyllithium in tetrahydrofuran; hexane T=-50 - 20°C; 1.25 h; 2: methyl iodide in tetrahydrofuran; hexane 5.25 h; Further stages.;

1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile T=20°C;

1: 93 percent / pyridine / CH2Cl2 / 20 °C 2: 100 percent / CH2Cl2 / 0.17 h / 20 °C 3: 88 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C View Scheme

1: 100 percent / CH2Cl2 / 0.17 h / 20 °C 2: 88 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 2.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 3.1: t-BuLi / tetrahydrofuran; pentane / 0.05 h / -110 - -40 °C 3.2: H2O / tetrahydrofuran; pentane / 20 °C 3.3: tetrahydrofuran; pentane / 3 h / 67 °C 4.1: 0.19 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1.25 h / -50 - 20 °C 1.2: 75 percent / hexane; tetrahydrofuran / 5.25 h 2.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 2.2: 71 percent / hexane; tetrahydrofuran / 5.25 h 3.1: t-BuLi / tetrahydrofuran; pentane / -110 - 20 °C 3.2: BrCH2CH2Br / tetrahydrofuran; pentane / -78 - 20 °C 4.1: 0.21 g / DIBAL-H / [NiCl2(dppp)] / toluene / 2 h / 20 °C View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -50 - 20 °C 1.2: 70 percent / hexane; tetrahydrofuran / 5.25 h 2.1: t-BuLi / tetrahydrofuran; pentane / 3.25 h / -110 - -40 °C 2.2: 75 percent / H2O / tetrahydrofuran; pentane / 20 °C View Scheme

1.1: 79 percent / cesium carbonate; BINAP / Pd2(dba)3 / toluene / 16 h / Heating 2.1: 94 percent / copper(I) chloride; potassium borohydride / methanol / 0.5 h / 20 °C 3.1: H2SO4; NaNO2 / H2O / 0.5 h / cooling 3.2: 60 percent / KI; copper / H2O / 0.5 h / Heating 4.1: t-BuLi / tetrahydrofuran; pentane / 0.83 h / cooling 4.2: 79 percent / methanol / tetrahydrofuran; pentane / 0.5 h / cooling View Scheme