Phosphorus pentachloride → HCID 57695508, compound

Participants

Reaction Steps

2,4-Bis-benzyloxy-5-bromo-N-(3-methoxy-propyl)-benzamide (3.3 g, 6.8 mmole) was dissolved in anhydrous dichloromethane (20 ml), then PCl5 (1.77 g, 8.2 mmol) was added and the resulting solution was stirred at r.t. for 3 h under nitrogen. The reaction mixture was then cooled to 0° C., and TMSN3 (6 ml, neat) was added at 0° C. and the resulting mixture was stirred at r.t. for 3 hr. After quenching the reaction with NaHCO3 solution, and the reaction mixture was extracted with dichloromethane (30 ml×3). The combined organic was dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 5-(2,4-bis-benzyloxy-5-bromo-phenyl)-1-(3-methoxy-propyl)-1H-tetrazole (2.8 g, 82%). M.p.: 92-93° C.; 400 MHz 1H NMR (CDCl3) δ: 7.68 (s, 1H), 7.44-7.31 (m, 8H), 7.19-7.15 (m, 2H), 6.64 (s, 1H), 5.17 (s, 2H), 4.99 (s, 2H), 4.28 (t, J=7.2 Hz, 2H), 3.22 (t, J=6.0 Hz, 2H), 3.16 (s, 3H), 2.03 (pent, J=6.4 Hz, 2H); LCMS: 509, 511 [M+H].

Provenance & Evidence