Ethyl Acetate → Ethyl 3-(1,5-naphthyridin-2-yl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

2-chloro-1,5-naphthyridine (101 mg, 0.614 mmol), boronate ester R1 (195 mg, 0.920 mmol), S-Phos (25.2 mg, 0.061 mmol), K3PO4 (391 mg, 1.841 mmol) and PdOAc2 (6.89 mg, 0.031 mmol) were combined in a 5-mL microwave vial in THF (2.5 mL) and water (500 μl). The reaction mixture was heated at 100° C. for 15 min. The reaction mixture was diluted with EtOAc (20 mL), washed with sat. aq. NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (10 to 100% EtOAc in hexanes) to afford the title compound as a pale orange solid (118 mg, 90%). 1H NMR (500 MHz, DMSO): δ 9.02 (dd, J=4.1, 1.6 Hz, 1 H), 8.48 (d, J=8.8 Hz, 1 H), 8.48-8.42 (m, 1 H), 8.25 (d, J=8.7 Hz, 1 H), 7.84-7.79 (m, 2 H), 7.13 (d, J=16.0 Hz, 1 H), 4.25 (q, J=7.1 Hz, 2 H), 1.30 (t, J=7.1 Hz, 3 H) ppm; LRMS m/z (M+H) 229.2 found, 229.1 required.

Provenance & Evidence