1,1'-Thiocarbonyldiimidazole → HCID 123678754, compound

Participants

Reaction Conditions

Reaction Steps

tert-butyl (3-(3-isothiocyanatopyridin-4-yl)-5-methylphenyl) carbamate. 1,1′-thiocarbonyldiimidazole (155 mg, 0.78 mmol, Sigma-Aldrich) was added to a solution of tert-butyl (3-(3-aminopyridin-4-yl)-5-methylphenyl)carbamate (117 mg, 0.39 mmol) in THF (4 mL) at RT. The reaction mixture was heated at 60° C. for 2 h. The mixture was cooled to RT, diluted with EtOAc, washed with water and the organic layer was dried over anh. Na2SO4, filtered and concentrated. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to provide tert-butyl (3-(3-isothiocyanatopyridin-4-yl)-5-methylphenyl)carbamate (63 mg, 0.19 mmol, 47% yield) as a white solid. MS (ESI, pos. ion) m/z: 342.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.58 (s, 1 H), 8.49 (d, J=5.09 Hz, 1 H), 7.32-7.37 (m, 2 H), 7.29 (s, 1 H), 6.98 (s, 1 H), 6.56 (s, 1 H), 2.41 (s, 3 H), 1.53 (s, 9 H).

Provenance & Evidence