Multi-step reaction with 6 steps
1: 28 percent / 3,5-dichloro-1-fluoropyridinium triflate / CH2Cl2 / 0.33 h / Heating
2: 67 percent / K2CO3 / dimethylformamide / 3.5 h / Ambient temperature
3: aq. KOH / methanol / 0.17 h / Ambient temperature
4: 1.) t-BuOK / 1.) DMF, 0 deg C, 5 min, 2.) DMF, from 0 deg C to RT
5: 1.) NaH, 2.) 18-crown-6 / 1.) diglyme, RT, 15 min, 2.) diglyme, reflux, 2 h
6: 98 percent / Zn, aq. AcOH / methanol; tetrahydrofuran / 0.5 h / Ambient temperature
With
potassium hydroxide; 18-crown-6 ether; potassium tert-butylate; sodium hydride; 1-fluoro-3,5-dichloropyridinium trifluoromethanesulfonate; potassium carbonate; acetic acid; zinc;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/jhet.5570350332