thionyl chloride 100 h; Heating;

1: Et3N / CH2Cl2 / 2 h / 0 °C 2: 1.) s-BuLi, 2.) B(OMe)3, 3.) Pd(PPh3)4, aq. Na2CO3 / 1) THF, -95 deg C, 10 min; 2) THF, -80 deg C, 2 h, -20 --> -10 deg C, overnight, rt, 1 h; 3) DME, reflux, 50 h 3: 95 percent / NaOH / methanol / 6 h / Heating 4: 1.) Et3N, diphenyl phosphorazidate, 2.) conc. HCl, phenol / 1) reflux, 22.5 h; 2) 110 deg C, 45 h 5: 100 percent / thionyl chloride / 100 h / Heating View Scheme

1: 1.) s-BuLi, 2.) B(OMe)3, 3.) Pd(PPh3)4, aq. Na2CO3 / 1) THF, -95 deg C, 10 min; 2) THF, -80 deg C, 2 h, -20 --> -10 deg C, overnight, rt, 1 h; 3) DME, reflux, 50 h 2: 95 percent / NaOH / methanol / 6 h / Heating 3: 1.) Et3N, diphenyl phosphorazidate, 2.) conc. HCl, phenol / 1) reflux, 22.5 h; 2) 110 deg C, 45 h 4: 100 percent / thionyl chloride / 100 h / Heating View Scheme

1: 95 percent / NaOH / methanol / 6 h / Heating 2: 1.) Et3N, diphenyl phosphorazidate, 2.) conc. HCl, phenol / 1) reflux, 22.5 h; 2) 110 deg C, 45 h 3: 100 percent / thionyl chloride / 100 h / Heating View Scheme

1: 1.) Et3N, diphenyl phosphorazidate, 2.) conc. HCl, phenol / 1) reflux, 22.5 h; 2) 110 deg C, 45 h 2: 100 percent / thionyl chloride / 100 h / Heating View Scheme