Compound 4h

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Compound data: HPLC

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a solution of 3k (0.1 mmol, 17.0 mg) in DMF (0.5 mL) were added 3-amino-1,2,4-triazole (0.2 mmol, 16.8 mg) and Cs₂CO₃ (0.3 mmol, 97.7 mg). The reaction mixture was stirred for 2 h at 100 ^oC. Upon completion, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The aqueous layer was back-extracted with ethyl acetate. The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The crude residue was purified by preparative TLC to afford 4h (11.0 mg, 51% yield, 68% ee). The ee value was determined by SFC analysis on a Chiralcel OJ-3 column (5% isopropanol, 2.0 mL/min) with retention time of 14.643 min (major) and 17.365 min (minor). ¹H NMR (600 MHz, CDCl₃): δ 9.62 (s, 1H), 8.52 (s, 1H), 8.51 (d, J = 8.1 Hz, 1H), 8.03 (t, J = 7.8 Hz, 1H), 7.72 (d, J = 8.2 Hz, 1H), 6.37 (dq, J = 46.6, 6.5 Hz, 1H), 1.91 (dd, J = 23.6, 6.6 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 154.31, 154.01 (d, J = 5.2 Hz), 152.61, 140.48 (d, J = 19.6 Hz), 136.51, 134.91, 123.33 (d, J = 9.2 Hz), 115.88, 115.86 (d, J = 1.7 Hz), 88.39 (d, J = 171.2 Hz), 23.26 (d, J = 24.6 Hz). ¹⁹F NMR (376 MHz, CDCl₃): δ –167.94. HRMS (ESI-TOF): m/z calculated for C₁₁H₁₀FN₄⁺ [M+H]⁺ 217.0884, found 217.0888.