N-bromobutanimide → Methyl 3-(bromomethyl)-6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245196Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=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]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[C:7]([O:22][CH3:23])[CH:6]=2.C1C(=O)N([Br:41])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:41][CH2:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:31])[F:33])[CH:25]=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]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[C:7]([O:22][CH3:23])[CH:6]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 3-methyl-6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.76 g, 3.66 mmol), NBS (0.846 g, 4.75 mmol) and diphenylperoxyanhydride (0.089 g, 0.366 mmol) in carbon tetrachloride (60 mL) was heated to 100° C. and stirred overnight. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure to afford methyl 3-(bromomethyl)-6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used in the next reaction without further purification. MS (m/z) 562.0 (M+H+).

Workup

temperatureThe mixture was cooled to room temperature
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-48d2e12859ff49d6b3c1a4da3c20dc8d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658636B2

Reaction notes

Loading…