alpha-Bromo-2-nitrotoluene → [4-{3-[(2-Nitrobenzyl)Oxy]Phenyl}-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)-Methanone

HRID 2104635Notes

Reaction equation

HRID 2104635 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N+:38]([O-:40])=[O:39]>CN(C=O)C>[N+:38]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:19])[F:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1)([O-:40])=[O:39]

Participants

4

Reactant 2

HCID 77569alpha-Bromo-2-nitrotolueneHCID 11773771[4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 66913573[4-{3-[(2-Nitrobenzyl)Oxy]Phenyl}-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)-MethanoneYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.15 g, 0.38 mmol), 1-Bromomethyl-2-nitro-benzene (0.10 g, 0.46 mmol) and CsCO3 (0.25 g, 0.76 mmol) in DMF (3 ml) was heated to 60° C. After 14 hr, the reaction was cooled, filtered and concentrated. The crude residue was purified by reverse phase HPLC to provide the desired compound (0.066 g, Yield=33%); MS (ESI) m/z 529;

Workup

  1. temperaturethe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a8e3de69eda8428cbe83da96e2cde74f
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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