1: 95 percent / n-BuLi / tetrahydrofuran / 10 h / -78 - 20 °C 2: 54 percent / conc. HCl / methanol / 3 h / Heating 4: 72 percent / n-BuLi / tetrahydrofuran; hexane / 7 h / -78 - 20 °C 5: 88 percent / NaI, trimethylsilyl chloride / acetonitrile / 3 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '110354', constants.ctx, '0')">4-(N,N-dimethlyamino)pyridine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587193', constants.ctx, '0')">bromine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605267', constants.ctx, '0')"><i>tert</i>-butylamine</a> <br />&nbsp;1.) toluene, CH₂Cl₂, -78 to RT, 5 h, 2.) pyridine, room temp., 24 h;&nbsp;&nbsp;Yield given. Multistep reaction;&nbsp;<br /> &nbsp;