1: H2 / 10percent Pd/C / acetonitrile / 4 h / 2068.6 Torr 2: MeONa / methanol / 3 h / Heating 3: LiBr / dimethylformamide / 4 h / Heating 4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, toluene, heating, 2 h View Scheme

1: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, 0 deg C, 4 h 2: H2 / 10percent Pd/C / acetonitrile / 4 h / 2068.6 Torr 3: MeONa / methanol / 3 h / Heating 4: LiBr / dimethylformamide / 4 h / Heating 5: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, toluene, heating, 2 h View Scheme

1: NaH / dimethylformamide / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, 0 deg C, 4 h 3: H2 / 10percent Pd/C / acetonitrile / 4 h / 2068.6 Torr 4: MeONa / methanol / 3 h / Heating 5: LiBr / dimethylformamide / 4 h / Heating 6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, toluene, heating, 2 h View Scheme

1: NaH / dimethylformamide / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, 0 deg C, 4 h 3: H2 / 10percent Pd/C / acetonitrile / 4 h / 2068.6 Torr 4: MeONa / methanol / 3 h / Heating 5: LiBr / dimethylformamide / 4 h / Heating 6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, toluene, heating, 2 h View Scheme

sodium hydride 1.) DMF, 20 min, 2.) DMF, toluene, 85 deg C, 4 h; Yield given. Multistep reaction;