1-Bromo-2-Chloroethane → HCID 57567594, compound

HRID 1727874Notes

Reaction equation

HRID 1727874 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][CH:17]=2)=[CH:11][C:10]=1[F:29])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][CH2:40][Cl:41]>CN(C)C=O>[Cl:41][CH2:40][CH2:39][O:28][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([O:15][C:12]3[CH:13]=[CH:14][C:9]([NH:8][C:6]([NH:5][CH2:4][CH2:3][C:2]([CH3:31])([CH3:30])[CH3:1])=[O:7])=[C:10]([F:29])[CH:11]=3)=[CH:17][CH:18]=[N:19]2)=[CH:24][C:23]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 136153639HCID 136153639, compound

Product 1

HCID 57567594HCID 57567594, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A crude product of 1-(3,3-dimethyl-butyl)-3-[2-fluoro-4-(7-hydroxy-6-methoxy-quinolin-4-yloxy)-phenyl]-urea was dissolved in dimethylformamide (100 ml) to prepare a solution. Potassium carbonate (18 g) and 1-bromo-2-chloroethane (11 g) were added to the solution, and the mixture was stirred at room temperature for 20 hr. The mixture was extracted with ethyl acetate, was then washed with saturated brine, and was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under the reduced pressure. The residue was washed with a mixed solvent of n-hexane: ethyl acetate (2:1) and was then collected by filtration to give 1-{4-[7-(2-chloroethoxy)-6-methoxy-quinolin-4-yloxy]-2-fluorophenyl}-3-(3,3-dimethyl-butyl)urea (7.7 g, yield 74%).

Workup

  1. customto prepare a solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwas then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by evaporation under the reduced pressure
  6. washThe residue was washed with a mixed solvent of n-hexane: ethyl acetate (2:1)
  7. filtrationwas then collected by filtration

Sources & evidence

ORD record
ord-99304b40a9a3438caafdea4a31372a88
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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