Boron tribromide → HCID 117600691, compound
Reaction equation
[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([NH2:16])=[CH:11][CH:12]=3)[C@@:7]3([CH2:21][CH2:20][O:19][C:18]([NH2:22])=[N:17]3)[C:6]=2[CH:5]=[C:4]([O:23]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:22][C:18]1[O:19][CH2:20][CH2:21][C@@:7]2([N:17]=1)[C:6]1[CH:5]=[C:4]([OH:23])[CH:3]=[C:2]([F:1])[C:15]=1[O:14][C:13]1[C:8]2=[CH:9][C:10]([NH2:16])=[CH:11][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The crude (S)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (1.196 g, 3.63 mmol) was dissolved in dcm (100 mL) and the solution was cooled to 0° C. A DCM solution of boron tribromide (14.53 mL, 14.53 mmol) was added, and the reaction was warmed to RT. After 1.5 h, the reaction was quenched with 120 mL of 10:1 saturated NH4Cl and commercial NH4OH. The mixture was extracted with 5% MeOH-DCM (3×250 mL). The organics were combined, washed with dilute brine (50 mL), dried over MgSO4 and concentrated, affording 0.97 g of crude (S)-2,7′-diamino-4′-fluoro-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2′-ol, which was used without purification in the next step. MS m/z=316 [M+H]+.
Workup
- temperaturethe reaction was warmed to RT
- customthe reaction was quenched with 120 mL of 10:1 saturated NH4Cl and commercial NH4OH
- extractionThe mixture was extracted with 5% MeOH-DCM (3×250 mL)
- washwashed with dilute brine (50 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1bf1154d8eba47b18ac3bd9156905533
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296759B2
Reaction notes
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