Sodium Carbonate → HCID 58465914, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave vial, the pyridin-3-ylboronic acid (0.061 g, 0.495 mmol), (S)-5-amino-2′-(5,6-dihydro-2H-pyran-3-yl)-4′-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthene]-7′-yl trifluoromethanesulfonate (0.196 g, 0.381 mmol), and Pd(PPh3)4 (0.044 g, 0.038 mmol) were suspended in dmf (4.1 mL). Aqueous sodium carbonate (1.0 M, 1.143 mL, 1.143 mmol) was added. Argon was blown through the vessel, which was sealed and heated in an 85° C. oil bath (11:40). After 1.5 h the reaction was concentrated. The residue was taken up in EtOAc (100 mL) and the organic layer was extracted with water (15 mL), brine (, then was dried over sodium sulfate and concentrated. The residue was purified by chromatography (7.5% MeOH/DCM) to afford (S)-2′-(5,6-dihydro-2H-pyran-3-yl)-4′-fluoro-7′-(pyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (99 mg, 0.22 mmol). MS (m/z) 444 (M+H)+. 1H NMR (400 MHz, CDCl3) δ ppm; 8.85 (s, 1H), 8.57 (d, 1H, J=4.5 Hz), 7.86 (d, 1H, J=8.0 Hz), 7.50 (m, 2H), 7.36 (m, 2H), 7.08 (dd, 1H, J=11.7, 2.0 Hz), 6.99 (s, 1H), 6.17 (s, 1H), 4.46 (m, 2H), 4.33 (s, 2H), 3.85 (t, 2H, J=5.7 Hz), 3.57 (m, 2H), 2.33 (m, 2H).

Provenance & Evidence