Benzoyl Peroxide → Methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245235Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:7][CH:6]=2.[Br:30]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (4.5 g, 10.63 mmol) in carbon tetrachloride (53.1 mL) was added N-bromosuccinimide (2.459 g, 13.82 mmol) and benzoyl peroxide (0.257 g, 1.063 mmol). The mixture was heated at 100° C. for 20 h, Additional portions of N-bromosuccinimide (0.3 equiv., 0.568 g, 3.19 mmol) and benzoyl peroxide (0.257 g, 1.063 mmol) were added, and the reaction mixture was heated at 100° C. for 5 h longer. The mixture was cooled to room temperature and concentrated in vacuo to give methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used in the next step without further purification. MS (m/z) 503.9 (M+H+).

Workup

temperaturethe reaction mixture was heated at 100° C. for 5 h longer
temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6a345c6b46fc4b90a16b996c362b6146
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658636B2

Reaction notes

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