Dichloromethane → HCID 67440104, compound

Participants

Reaction Steps

To a suspension of 4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (2.178 g, 5.32 mmol) in DCM (43 mL) boron tribromide (1.509 mL, 15.96 mmol) was added dropwise at RT. The mixture was stirred 2 hrs at RT, the mixture was cooled to 0° C. and quenched by addition of 5 ml of methanol dropwise. The resulting white suspension was stirred for 20 min at 0° C., then sat. aq. NaHCO3 (˜5 ml) was added followed by addition of 25% aq. ammonia (˜15 ml). The mixture was stirred for 30 min, then DCM was removed in a stream of nitrogen. The mixture was diluted with water (10 ml) and 25% ammonia (10 ml) and filtered. The white solid was washed with water twice, then dried for 3 hrs on air, then in vacuo overnight to give 2-amino-4′-fluoro-7′-(2-fluoropyridin-3-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2′-ol (2.08 g, 5.26 mmol, 99% yield).

Provenance & Evidence