Sodium percarbonate → 7-(Bromomethyl)-4-(4-fluorophenyl)-2-quinolinecarboxamide

HRID 922759Notes

Reaction equation

HRID 922759 reaction equation
C([O-])([O-])=[O:2].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].[Br:19][CH2:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:26][C:27]([C:31]#[N:32])=[N:28]2)=[CH:23][CH:22]=1>O.CC(C)=O>[Br:19][CH2:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:26][C:27]([C:31]([NH2:32])=[O:2])=[N:28]2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 159762Sodium percarbonateHCID 194270117-(Bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile

Product 1

HCID 895440027-(Bromomethyl)-4-(4-fluorophenyl)-2-quinolinecarboxamideYield 57.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Sodium percarbonate (2.98 g, 9.50 mmol, 3.0 equiv.) in water (52.8 ml) was added dropwise to a solution of 7-(bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile (2-1, 1.08 g, 3.17 mmol, 1.0 equiv.) in acetone (106 ml) and the reaction stirred for 1 hour at rt. The reaction was quenched with saturated KH2PO4 and the mixture was extracted with EtOAc (3×). The combined organic fractions were dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography (120 g SiO2, 0-100% EtOAc/hexanes) to afford 7-(bromomethyl)-4-(4-fluorophenyl)quinoline-2-carboxamide (3-1, 650 mg, 57%) as a white solid. LRMS m/z (M+H)+ 359.05 found, 359.19 required.

Workup

  1. customThe reaction was quenched with saturated KH2PO4
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography (120 g SiO2, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-094e8cd2ba0248fd9d76f22b6b90a12a
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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