Iodoethane → HCID 131721992, compound

HRID 1953850Notes

Reaction equation

HRID 1953850 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:17]([CH2:29][CH3:30])=[N:18][C:19]3[C:24]([C:25]=2[C:26]([OH:28])=[O:27])=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][CH:10]=1)#[N:2].[CH2:31](I)[CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.CC(C)=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[C:17]([CH2:29][CH3:30])=[N:18][C:19]3[C:24]([C:25]=2[C:26]([O:28][CH2:31][CH3:32])=[O:27])=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:14]=1)#[N:2]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 23298209HCID 23298209, compound

Product 1

HCID 131721992HCID 131721992, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture containing the title C compound of Example 2, 3-[(2'-cyano[1,1'-biphenyl]-4-yl)oxy]-2-ethyl-4-quinolinecarboxylic acid (707 mg, 1.79 mmol), ethyl iodide (559 mg, 3.58 mmol), and cesium carbonate (1.46 g, 4.48 mmol) in dimethylformamide (4 mL) was stirred at room temperature for nine hours, then diluted with a mixture of acetone and ethyl acetate and filtered. The filtrate was concentrated in vacuo and the product extracted into ethyl acetate. The organic extract was rinsed with water and brine, dried (magnesium sulfate), and concentrated in vacuo to afford a crude product (720 mg). Flash chromatography on Merck silica gel (30 g) eluted with 1:1 hexanes:ethyl acetate afforded the title compound (703 mg, 93% yield).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. extractionthe product extracted into ethyl acetate
  4. extractionThe organic extract
  5. washwas rinsed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto afford a crude product (720 mg)
  9. washFlash chromatography on Merck silica gel (30 g) eluted with 1:1 hexanes

Sources & evidence

ORD record
ord-b26bcd5120db4873934d1f99ee7089e2
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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