Ethyl bromoacetate → HCID 91376496, compound

Participants

Reaction Steps

Iso-nicotinic hydrazide (1.0 g, 7.3 mmol), 3,5-dichlorobenzonitrile (1.5 g, 8.8 mmol), and sodium ethoxide (1.5 g, 22 mmol) were transferred to a pressure tube. Ethanol (4 mL) was added and the reaction was stirred at 120° C. overnight. The reaction was monitored by LCMS. Upon completion, the ethanol was removed in vacuo to afford the triazole as a solid and carried on to the next step without purification. This material was dissolved in DMF (10 mL), and potassium carbonate (1.5 g, 11 mmol) and ethyl bromoacetate (1.2 mL, 11 mmol) were added. The reaction was stirred at room temperature overnight. The reaction was monitored by LCMS. Upon completion, the reaction mixture was diluted with water. The precipitate was collected via vacuum filtration and the filtrate was discarded. The crude product was purified by silica gel chromatography (3:2 hexanes/ethyl acetate) to afford two regioisomers as solids. 1H NMR (400 MHz, d6-DMSO): δ 8.7 (d, 21, 7.95 (s, 2H), 7.9 (d, 1H), 7.8 (d, 2H), 5.5 (s, 2H), 4.1 (q, 2H), 1.1 (t, 3H). MS (EI) for C17H14N4O2Cl2: 377 (MH+). Ethyl[3-(3,5-dichlorophenyl)-5-pyridin-4-yl-1H-1,2,4-triazol-1-yl]acetate: 1H NMR (400 MHz, d6-DMSO): δ 8.8 (d, 2H), 8.0 (s, 2H), 7.8 (m, 3H), 5.5 (s, 2H), 4.1 (q, 2H), 1.2 (t, 3H). MS (EI) for C17H14N4O2Cl2: 377 (MH+).

Provenance & Evidence