Hydrochloric Acid → HCID 44621524, compound

Participants

Reaction Steps

A mixture of 1-iodo-4-isopropylbenzene (5-1) (123 mg, 0.5 mmol), sodium azide (34 mg, 0.52 mmol), 3-ethynylbenzoic acid (5-2) (73 mg, 0.5 mmol), CuI (10 mg), MeNHCH2CH2NHMe (11 μL), Et3N (51 mg, 0.5 mmol), sodium ascorbate (10 mg), DMSO-H2O (v/v 5:1, 1.5 mL) is stirred at room temperature for 2 hours followed by the addition of 2 mL of 1M HCl. The resulting mixture is poured into ethyl acetate (100 mL), washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue is purified on silica gel (0-100% ethyl acetate in hexane) to give 3-[1-(4-isopropylphenyl)-1H-1,2,3-triazol-4-yl]benzoic acid (5-3) as a white solid. 1H NMR (DMSO-d6) δ (ppm) 9.42 (s, 1H), 8.53 (dd, J=1.6, 1.6 Hz, 1H), 8.20 (ddd, J=8.0, 1.6, 1.2 Hz, 1H), 7.95 (ddd, J=8.0, 1.6, 1.2 Hz, 1H), 7.89 (dm, J=8.8 Hz, 2H), 7.64 (dd, J=8.4, 8.0 Hz, 1H), 7.51 (dm, J=8.8 Hz, 2H), 3.00 (septet, J=6.8 Hz, 1H), 1.26 (d, J=6.8 Hz, 6H). HPLC-MS calculated for C18H17N3O2 (M+H+) 308.13. found 308.10.

Provenance & Evidence