N-bromobutanimide → HCID 67383469, compound

HRID 245226Notes

Reaction equation

HRID 245226 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][CH:8]=[C:7]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:6]=2.C1C(=O)N([Br:37])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:37][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][CH:8]=[C:7]([S:16]([CH3:19])(=[O:17])=[O:18])[CH:6]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67383916HCID 67383916, compound

Product 1

HCID 67383469HCID 67383469, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3-methyl-7-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.20 g, 2.83 mmol), NBS (0.656 g, 3.68 mmol), and diphenylperoxyanhydride (0.069 g, 0.283 mmol) in carbon tetrachloride (20 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)-7-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used directly in the next step without further purification. MS (m/z) 504.0 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-816b7a15a34545e79a1fb442b85212f5
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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