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

HRID 245253Notes

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.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:55])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:55][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

A mixture of methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2 g, 4.72 mmol), benzoyl peroxide (0.114 g, 0.472 mmol) and NBS (1.093 g, 6.14 mmol) was suspended in carbon tetrachloride (31.5 mL) and heated to reflux for 4 h. Additional benzoyl peroxide (0.571 g, 2.36 mmol) was added, and the mixture was stirred at 100° C. for 24 h. Additional benzoyl peroxide (0.571 g, 2.36 mmol) was added, and the mixture stirred for 3 h. Additional benzoyl peroxide (0.571 g, 2.36 mmol) and NBS (0.250 g, 1.42 mmol) were added, and the mixture was heated for 2.5 h. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure to afford methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used without further purification. MS (m/z) 502.0 (M+H+).

Workup

temperatureheated
temperatureto reflux for 4 h
stirringthe mixture stirred for 3 h
temperaturethe mixture was heated for 2.5 h
temperatureThe mixture was cooled to room temperature
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-f8e23f21d5274db9951ff5adc230ff27
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658636B2

Reaction notes

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