Sodium Azide → HCID 117600285, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (422 mg, 1.073 mmol) in ethanol (3.5 ml) was added sodium azide (209 mg, 3.22 mmol), copper(I) iodide (41 mg, 0.215 mmol), (+)-sodium L-ascorbate (21 mg, 0.107 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (0.05 ml, 0.322 mmol) and water (1.5 ml) and the mixture was stirred at 90° C. for 4 hrs. The mixture was cooled to RT, additional water (2 ml) was added and stirring continued for additional 30 min. Precipitated material was filtered off, washed with water twice, and dried under a stream of nitrogen overnight to afford (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (290 mg, 0.816 mmol, 76% yield) which was used without further purification.

Provenance & Evidence