Multi-step reaction with 6 steps
1: 60 percent / chlorosulfonyl isocyanate / CH2Cl2 / 0.75 h / Heating
2: 65 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.25 h / Heating; Irradiation
3: 24 percent / dimethylformamide / 1.) 0 deg C, 15 min, 2.) RT, 4.25 h
4: 98 percent / sodium azide, Et3N*HCl, N-methylpyrrolidone (NMP) / 3 h / 150 °C
5: 79 percent / H2, 6 M KOH / 10percent Pd/C / methanol / 2 h / 825.07 Torr
6: 66 percent / 2,6-lutidine, N-methylpyrrolidone (NMP) / tetrahydrofuran / 1.) from 0 deg C to RT, 2 h, 2.) RT, 14 h
With
2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; potassium hydroxide; N-Bromosuccinimide; sodium azide; Perbenzoic acid; isocyanate de chlorosulfonyle; hydrogen; triethylamine hydrochloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00171a018