1,8-Diazabicyclo(5.4.0)undec-7-ene → 6,7-Difluoro-2-[4-(trifluoromethyl)pyridin-3-yl][1,2,4]triazolo[1,5-a]pyridine

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Reaction Steps

4-(trifluoromethyl)nicotinaldehyde was added to a solution of 1,2-diamino-4,5-difluoropyridinium 2,4,6-trimethylbenzenesulfonate (47-4; 0.2 g, 0.000579 mol) in ethanol (20 mL) while stirring, followed by the addition of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was stirred for 12 h at RT. It was then concentrated under vacuum, diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The collected organic parts were concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compounds. 1H NMR (400 MHz, DMSO) δ 8.20 (s, 1H), 9.09-9.06 (m, 1H), 9.03-9.02 (d, J=4 Hz, 1H), 7.99-7.77 (d, J=8 Hz, 1H), 7.61-7.55 (m, 1H). HPLC purity-99.13%, MS (M+1): 301.1.

Provenance & Evidence