Boron tribromide → HCID 136414048, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]4[CH2:24][CH2:23][CH2:22][C@@H:21]4[CH3:25])=[N:18][C:17]4[C:12](=[CH:13][C:14]([O:30]C)=[C:15]([C:26]([O:28][CH3:29])=[O:27])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.B(Br)(Br)Br>ClCCl>[OH:30][C:14]1[CH:13]=[C:12]2[C:17]([N:18]=[C:19]([N:20]3[CH2:24][CH2:23][CH2:22][C@@H:21]3[CH3:25])[C:10]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[NH:1][N:2]=[CH:3]4)=[N:11]2)=[CH:16][C:15]=1[C:26]([O:28][CH3:29])=[O:27]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -60 °C
Procedure
To a solution of (S)-methyl 2-(1H-indazol-5-yl)-7-methoxy-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (208 mg, 0.50 mmol) in dichloromethane (20 ml) was added BBr3 (0.37 g, 0.75 mmol) at −60° C. The resulting solution was stirred for 0.5 h at −60° C. The reaction was then quenched by the addition of water/ice (200 ml), extracted with dichloromethane (4×50 ml), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated under vacuum to give the residue, which was purified via silica gel chromatography (10% ethyl acetate in petroleum ether) to afford (S)-methyl 7-hydroxy-2-(1H-indazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a yellow solid (180 mg, 90%).
Workup
- customThe reaction was then quenched by the addition of water/ice (200 ml)
- extractionextracted with dichloromethane (4×50 ml)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under vacuum
- customto give the residue, which
- customwas purified via silica gel chromatography (10% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-3913634fa9844751bef594d806d744fe
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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