Compound 4g

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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 DMA (0.5 mL) was added guanidine carbonate salt (0.25 mmol, 22.5 mg). The reaction mixture was stirred for 1 h at 150 ^oC. Upon completion, the reaction mixture was diluted with ethyl acetate and washed with sat. Na₂CO₃ (aq), 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 4g (9.1 mg, 48% yield, 95% ee). The ee value was determined by SFC analysis on a Chiralcel OD-3 column (5% isopropanol, 2.0 mL/min) with retention time of 10.408 min (minor) and 11.633 min (major). ¹H NMR (600 MHz, CDCl₃): δ 9.38 (s, 1H), 7.68 (t, J = 7.8 Hz, 1H), 7.56 (d, J = 8.5 Hz, 1H), 7.29 (d, J = 7.4 Hz, 1H), 6.20 (dq, J = 46.8, 6.6 Hz, 1H), 5.23 (br s, 2H), 1.83 (dd, J = 23.6, 6.5 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 159.71, 159.15 (d, J = 5.1 Hz), 152.64, 138.30 (d, J = 18.9 Hz), 133.81, 126.42 (d, J = 1.7 Hz), 120.13 (d, J = 8.8 Hz), 117.32 (d, J = 2.1 Hz), 88.62 (d, J = 168.6 Hz), 22.77 (d, J = 24.7 Hz). ¹⁹F NMR (376 MHz, CDCl₃): δ –166.89.HRMS (ESI- TOF): m/z calculated for C₁₀H₁₁FN₃⁺ [M+H]⁺ 192.0932, found 192.0931.