Water → HCID 68194082, compound

HRID 1520150Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:28]([O:30][CH3:31])=[O:29])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:39])C(=O)C1.O>CN(C)C=O>[Br:39][C:24]1[CH:23]=[C:22]2[C:27](=[CH:26][CH:25]=1)[N:18]([C:17]1[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][C:10]3[C:15]([N:16]=1)=[CH:14][C:13]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][CH:11]=3)[CH2:19][CH2:20][CH2:21]2

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (300 mg, 0.73 mmol) in N,N-dimethylformamide (20 ml) was added NBS (193 mg, 1.08 mmol) under an inert atmosphere of nitrogen. The resulting solution was stirred for 1.5 h at −10° C. Then water (150 ml) was added and the reaction was extracted with ethyl acetate (3×50 ml). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel chromatography eluting with 1%-2% ethyl acetate in petroleum ether to afford methyl 3-(6-bromo-1,2,3,4-tetrahydroquinolin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (200 mg, 56%).

Workup

extractionthe reaction was extracted with ethyl acetate (3×50 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by silica gel chromatography
washeluting with 1%-2% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-850748d1fac341deb1ebd84d177a1b11
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073902B2

Reaction notes

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