hydrazine hydrate; Ti(O-IPr)4 in dichloromethane

1: 1.) lithium diisopropylamide*THF complex / 1.) cyclohexane, -65 deg C, 2.) THF, cyclohexane, -65 deg C, 30 min 2: titanium(IV) isopropoxide, hydraziner hydrate / CH2Cl2 / 1 h 3: NaH / tetrahydrofuran / 0.33 h View Scheme

1: titanium(IV) isopropoxide, hydraziner hydrate / CH2Cl2 / 1 h 2: NaH / tetrahydrofuran / 0.33 h View Scheme

1: tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate With sodium hydride in tetrahydrofuran T=0°C; 0.5 h; 2: methyl iodide in tetrahydrofuran 1 h;