Trifluoroacetic acid → HCID 22347604, compound

Participants

Reaction Steps

To a solution of 2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-1-ethanol (0.17 g, 0.96 mmol) and polymer bound PPh3 (0.32 g, 0.96 mmol) in dry THF (10 mL) was added ethyl [2,2-dibromo-3-(4-hydroxyphenyl)cyclopropyl]acetate (0.18 g, 0.6 mmol) followed by diisopropyl azodicarboxylate (0.2 mL, 1 mmol). The reaction mixture was stirred at room temperature. After 18 hours, polymer was filtered through Celite and washed with excess THF. Filtrate was concentrated. The concentrated residue in 50% acetonitrile in water (4 mL) was added LiOH (0.14 g). The reaction mixture was stirred 3 hours at room temperature. Reaction mixture was acidified by adding TFA and purified by reverse phase HPLC to afford 50 mg (12%) of desired product. 1H NMR (CD3OD) δ 7.59 (d, 1H, J=7.4 Hz), 7.21 (d, 2H, J=8.6 Hz), 6.88 (d, 2H, J=8.7 Hz), 6.73 (d, 1H, J=7.2 Hz), 4.27 (t, 2H, J=6.0 Hz), 3.49 (t, 2H, J=5.9 Hz), 3.14 (t, 2H, J=5.9 Hz), 2.82-2.78 (m, 3H), 2.71-2.59 (m, 2H), 2.25-2.19 (m, 1H), 1.97-1.90 (m, 2H). HRMS calcd for C21H22N2O3 (M+H): 421.1080. found 421.1069.

Provenance & Evidence