Sodium Carbonate → HCID 117600815, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave vial, 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.107 g, 0.509 mmol) and Pd(PPh3)4 (0.053 g, 0.046 mmol) were loaded. A solution of (S)-2,2′-diamino-5′-fluoro-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-7′-yl trifluoromethanesulfonate (0.207 g, 0.463 mmol) in dmf (3.7 mL) was added via cannula. Aqueous 1.5 M sodium carbonate (0.925 mL, 1.388 mmol) was added. Argon was blown through the vessel, which was sealed and heated in an 85° C. oil bath. After 4 h, the reaction was concentrated. The residue was taken up in EtOAc (100 mL) and the organic layer was extracted with quarter-saturated brine (2×8 mL), half-saturated brine (8 mL), and saturated brine (8 mL), dried over MgSO4 and concentrated. The material was purified through silica gel (35 mL) which had been deactivated with Et3N (3.5 mL), using a gradient of 3% to 6% MeOH-dcm with 0.5% v/v Et3N, affording (S)-2′-(3,6-dihydro-2H-pyran-4-yl)-4′-fluoro-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (48 mg, 0.126 mmol). MS m/z=382 [M+H]1.

Provenance & Evidence