Related Products of 151899-62-6, A common heterocyclic compound, 151899-62-6, name is 3-Iodo-1-trityl-1H-1,2,4-triazole, molecular formula is C21H16IN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Nitrogen gas was bubbled through a solution of (15)-3-[(25r,3lambda)-2-(4-{4- (acetyloxy)-3 – [(acetyloxy)methyl] -3 -hydroxybut- 1 -yn- 1 -yl } phenyl)- 1 -(4-ethynylphenyl)-4- oxoazetidin-3-yl]-l-(4-fluorophenyl)propyl acetate (4.Og, 6.3mmol; intermediate step B), 3-iodo- l-trityl-lH-l,2,4-triazole (i-8) (5.47g, 12.5mmol), triethylamine (4.4mL, 31.3mmol), and tetra-n- butylammonium iodide (2.3 Ig, 6.3mmol) in anhydrous DMF (5mL) and was heated at 5O0C for 20 minutes. Pd(PPh3)4 (0.72g, 0.63mmol) and CuI (0.2g, 1.25mmol) were added and the reaction mixture was heated at 5O0C under nitrogen atmosphere for ~18hr. The reaction mixture was cooled to RT, poured into water (70OmL) and extracted with EtOAc (3x200mL). The combined organic layers were washed with water (2x500mL), brine (20OmL) dried over Na2SO4,10 filtered and the solvent removed under vacuum. The residue was purified by column chromatography eluting with 0%EtOAc/hexanes then gradient from 0%EtOAc/hexanes to 50%EtOAc/hexanes then 50% EtOAc/hexanes to 60% EtOAc/hexanes then 60% EtOAc/hexanes to afford the title compound. 1HNMR (500 MHz, CDCl3) delta: 8.03 (s, IH), 7.45 (d, J = 8.0, 2H), 7.44 (d, J = 8.7, 2H), 7.36 (m, 9H), 7.29 (m, 4H), 7.19 (d, J – 8.7, 2H), 7.15 (m, 6H), 7.04 (t, J =15 8.4, 2H), 5.71 (t, J – 6.6, IH), 4.63 (d, J = 2.3, IH), 4.39 (d, J = 11.5, 2H), 4.32 (d, J = 11.5, 2H), 3.36 (s, IH), 3.08 (m, IH), 2.15 (s, 6H), 2.07 (s, 3H), 2.07-2.02 (m, 2H), 1.93-1.85 (m, 2H).
The synthetic route of 151899-62-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK & CO., INC.; WO2008/57336; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics