Boron tribromide → 5-Amino-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-2'-ol
Reaction equation
[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:16]4[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:11][CH:12]=3)[C:7]3([N:27]=[C:26]([NH2:28])[CH2:25][O:24][CH2:23]3)[C:6]=2[CH:5]=[C:4]([O:29]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:28][C:26]1[CH2:25][O:24][CH2:23][C:7]2([C:6]3[CH:5]=[C:4]([OH:29])[CH:3]=[C:2]([F:1])[C:15]=3[O:14][C:13]3[C:8]2=[CH:9][C:10]([C:16]2[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][CH:12]=3)[N:27]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (1.668 g, 4.07 mmol) in DCM (12 ml) was added boron tribromide (0.963 mL, 10.19 mmol) at 0° C. The reaction mixture was stirred for 45 hrs at 0° C. The reaction mixture was allowed to warm to RT and was stirred for additional 2 hrs. The reaction mixture was cooled to 0° C. and quenched by addition of saturated aqueous NaHCO3 solution (˜10 mL). The solvent was removed in vacuo, the mixture was diluted with water and filtered. The solid was washed with water and dried under reduced pressure to afford 5-amino-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-2′-ol (1.53 g, 3.87 mmol, 95% yield).
Workup
- temperatureto warm to RT
- stirringwas stirred for additional 2 hrs
- temperatureThe reaction mixture was cooled to 0° C.
- customquenched by addition of saturated aqueous NaHCO3 solution (˜10 mL)
- customThe solvent was removed in vacuo
- additionthe mixture was diluted with water
- filtrationfiltered
- washThe solid was washed with water
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-b8a02fa966404a538cdc27cf936046e8
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497264B2
Reaction notes
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