Boron tribromide → HCID 136414050, compound

HRID 1403593Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][C:12]([O:27]C)=[C:13]([C:23]([O:25][CH3:26])=[O:24])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([N:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[N:16][C:15]3[C:10](=[CH:11][C:12]([OH:27])=[C:13]([C:23]([O:25][CH3:26])=[O:24])[CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(isopropyl(methyl)amino)-7-methoxyquinoxaline-6-carboxylate (500 mg, 1.31 mmol) in dichloromethane (80 mL) was added BBr3 (2.0 mL) dropwise with stirring at −78° C. for 30 minutes. The reaction was then quenched by the addition of water/ice. The resulting solution was extracted with dichloromethane (3×80 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 2-(4-fluorophenyl)-7-hydroxy-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid (145 mg, 30%).

Workup

customThe reaction was then quenched by the addition of water/ice
extractionThe resulting solution was extracted with dichloromethane (3×80 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto give the residue, which
customwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-cbff7afd8f4e4f608e5b3d9c123b38ad
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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