Quinoline → HCID 11208671, compound

HRID 1988105Notes

Reaction equation

HRID 1988105 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]2[CH:1]=[CH2:2])=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7047QuinolineHCID 85014-Chlorobenzoyl chlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 11208671HCID 11208671, compound

Conditions

Temperature
40 °C

Procedure

A solution of vinyl magnesium bromide (4.65 mL in 1M THF solution) under nitrogen gas at ambient conditions is treated with quinoline dropwise. The reaction mixture is warmed to 40° C. and stirred for 1 h. The reaction mixture is then allowed to attain ambient conditions and 4-chlorobenzoyl chloride (591 μL) is then added dropwise and reaction mixture stirred overnight. The reaction mixture is then cooled to 0° C. and quenched with saturated aqueous ammonium chloride solution. The reaction mixture is then partitioned between diethyl ether and water and the organic layer is washed successively with 1N hydrochloric acid and 1N sodium hydroxide solution and then dried over sodium sulfate. The organic solvent is removed under reduced pressure and the crude product is purified by liquid chromatography (gradient elution of acetonitrile (0.02% trifluoroacetic acid/water (0.02% trifluoroacetic acid) through a reverse phase. (M+H)+−296.

Workup

  1. additionis then added dropwise
  2. customreaction mixture
  3. stirringstirred overnight
  4. temperatureThe reaction mixture is then cooled to 0° C.
  5. customquenched with saturated aqueous ammonium chloride solution
  6. customThe reaction mixture is then partitioned between diethyl ether and water
  7. washthe organic layer is washed successively with 1N hydrochloric acid and 1N sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. customThe organic solvent is removed under reduced pressure
  10. customthe crude product is purified by liquid chromatography (
  11. washgradient elution of acetonitrile (0.02% trifluoroacetic acid/water (0.02% trifluoroacetic acid) through a reverse phase

Sources & evidence

ORD record
ord-bfad87ee4fb64a249c08383031697970
Source dataset
uspto-grants-2009_06
Patent number
US07553967B2

Reaction notes

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