Boron tribromide → (E)-5-amino-7'-bromo-4'-fluoro-6,7-dihydro-2H-spiro[[1,4]oxazepine-3,9'-xanthen]-2'-ol

A solution of (E)-7′-bromo-4′-fluoro-2′-methoxy-6,7-dihydro-2H-spiro[[1,4]oxazepine-3,9′-xanthen]-5-amine (0.990 g, 2.431 mmol) in DCM (24.31 mL) was cooled in an ice-bath for 5 min. Boron tribromide (0.919 mL, 9.72 mmol) was added dropwise to give a resulting brown mixture. The mixture was stirred for 1 h, at which time a saturated aq. sodium bicarbonate solution (25 mL) was added. The mixture was stirred for 5 min. and concentrated on a rotary evaporator to remove the DCM. The mixture was heated with a heat gun for 5 min, and at this point the solid was scraped from the sides of the flask. The flask was sonicated for 1 min, then reheated for 2 min. The flask was again sonicated for 1 min, then cooled to RT. The solid was filtered. The filter cake was washed twice with water, then air-dried under a stream of N2 (g) for 1.5 h to give (E)-5-amino-7′-bromo-4′-fluoro-6,7-dihydro-2H-spiro[[1,4]oxazepine-3,9′-xanthen]-2′-ol as a light-yellow solid. The solid was used without further purification.

1. customto give a resulting brown mixture
2. additionwas added
3. concentrationconcentrated on a rotary evaporator
4. customto remove the DCM
5. temperatureThe mixture was heated with a heat gun for 5 min
6. customThe flask was sonicated for 1 min
7. waitreheated for 2 min
8. customThe flask was again sonicated for 1 min
9. filtrationThe solid was filtered
10. washThe filter cake was washed twice with water
11. dry with materialair-dried under a stream of N2 (g) for 1.5 h

ORD-Eintrag

ord-e377021e77924aacbf10d7e7abba4c35

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09346827B2