2,4,6-trimethyl-pyridine; methanesulfonyl chloride; lithium chloride in N,N-dimethyl-formamide 1) 0 deg C, 20 min, 2) 4 h, RT;

1: 90 percent / LiNH2, NH3 / 4 h 2: 1.) CH3SO2Cl, Et3N, 2.) LiCl / 1.) CH2Cl2, -40 deg C, 4 h, room temperature, 2.) DMF, 60 deg C to room temperature, 12 h View Scheme

1: 90 percent / p-TsOH / methanol / 30 h / Ambient temperature 2: 85 percent / MsCl, LiCl, sym-collidine / dimethylformamide / 1) 0 deg C, 20 min, 2) 4 h, RT View Scheme