Potassium Phosphate, Tribasic → HCID 71061072, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)boronic acid (PP1) (25 mg, 0.050 mmol), 5-bromo-2,4-dimethyl-1,3-thiazole (9.6 mg, 0.050 mmol), K3PO4 (21.2 mg, 0.10 mmol), S-Phos (2.0 mg, 0.005 mmol), and Pd(OAc)2 (0.6 mg, 0.002 mmol) in THF (0.3 mL) and water (0.05 mL) was heated at 100° C. for 14 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (5 mL), washed with sodium bicarbonate (1 mL) and brine (1 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by reverse phase chromatography (Waters Sunfire Prep C18 OBD, 5-45% acetonitrile in water with 0.1% TFA modifier) to afford the title compound. 1H NMR (500 MHz, DMSO): δ 8.83 (dd, J=4.2, 1.6 Hz, 1 H), 8.29 (s, 1 H), 8.20 (d, J=8.5 Hz, 1 H), 8.12 (d, J=2.9 Hz, 1 H), 7.71 (dd, J=8.4, 4.2 Hz, 1 H), 7.30-7.23 (m, 2 H), 4.61 (dd, J=11.3, 6.7 Hz, 1 H), 4.39 (dd, J=11.3, 7.8 Hz, 1 H), 3.78 (s, 3 H), 2.61 (s, 3 H), 2.36 (s, 3 H), 2.20 (dt, J=8.5, 4.6 Hz, 1 H), 1.79 (s, 1 H), 1.24 (s, 1 H), 1.09-1.04 (m, 1 H); HRMS m/z (M+H) 418.1534 found, 418.1536 required.

Provenance & Evidence