Dimethylformamide → 6-Bromo-4-chloro-3-(4-chlorophenoxy)-2-(3-isopropoxyazetidin-1-yl)quinoline

HRID 520845Notes

Reaction equation

HRID 520845 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:5]2O.CN(C)C=O.[ClH:27].[CH:28]([O:31][CH:32]1[CH2:35][NH:34][CH2:33]1)([CH3:30])[CH3:29]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:34]1[CH2:35][CH:32]([O:31][CH:28]([CH3:30])[CH3:29])[CH2:33]1)[C:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:5]2[Cl:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 532491903-Isopropoxyazetidine hydrochlorideHCID 867154546-Bromo-3-(4-chlorophenoxy)-4-hydroxyquinolin-2(1H)-one2×

Product 1

HCID 1180054806-Bromo-4-chloro-3-(4-chlorophenoxy)-2-(3-isopropoxyazetidin-1-yl)quinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 6-bromo-2,4-dichloro-3-(4-chlorophenoxy)quinoline (0.50 g, 1.24 mmol, Intermediate 7: step c) was added N,N-dimethylformamide (3 mL) and 3-isopropoxyazetidine-HCl (0.188 g, 1.24 mmol), and the reaction was heated at 60° C. overnight. The reaction was cooled, diluted with ethyl acetate and the organic layer was washed with water five times to remove the N,N-dimethylformamide. The organic layer was dried (MgSO4), filtered and concentrated, then purified over a silica gel column with ethyl acetate/heptane to afford the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. washthe organic layer was washed with water five times
  3. customto remove the N,N-dimethylformamide
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified over a silica gel column with ethyl acetate/heptane

Sources & evidence

ORD record
ord-324eb254ef594e5dba337758e0e6ef4e
Source dataset
uspto-grants-2016_05
Patent number
US09328095B2

Reaction notes

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