Water → (S)-5-amino-2'-(5,6-dihydro-2H-pyran-3-yl)-4'-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-7'-ol

Participants

Reaction Conditions

Reaction Steps

In a microwave vial, the potassium phosphate (0.771 g, 3.63 mmol), PdCl2(AmPhos)2 (0.064 g, 0.091 mmol) and 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.356 g, 1.695 mmol) were loaded. The (S)-5-amino-2′-bromo-4′-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-7′-ol (0.459 g, 1.211 mmol) was added as a solution in dioxane (6 mL). Water (2.4 mL) was added and argon gas was blown through the vessel, which was sealed and heated by microwave at 120° C. for 30 min. The residue was taken up in half-saturated aqueous NH4Cl (30 mL) and the aqueous phase was extracted with 5% MeOH/DCM (3×25 mL). The organics were combined, washed with brine (7 mL), dried over sodium sulfate and concentrated to afford crude (S)-5-amino-2′-(5,6-dihydro-2H-pyran-3-yl)-4′-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-7′-ol which was used directly in the next step.

Provenance & Evidence