Dimethylformamide → HCID 23078424, compound

HRID 228851Notes

Reaction equation

HRID 228851 reaction equation
CN(C)C=O.Br[C:7]1[C:16]([O:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.C([Sn](CCCC)(CCCC)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)CCC>[Cu]=O.O>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:17][C:16]1[C:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6077842-(Tributylstannyl)pyridineHCID 23078407HCID 23078407, compound

Product 1

HCID 23078424HCID 23078424, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

N,N-Dimethylformamide (1 ml) was added to 4-(2-bromo-quinolin-3-yloxy)-6,7-dimethoxy-quinoline (35 mg), tetrakistriphenylphosphine palladium (9.8 mg), tri-n-butyl-(2-pyridyl)-tin (63 mg), and copper(II) oxide (14 mg) under an argon atmosphere, and the mixture was stirred at 100° C. overnight. The reaction solution was cooled to room temperature, water was then added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-acetone. The purification product was then dissolved in methanol, and the solution was added dropwise to water. The precipitate was collected by filtration to give the title compound (5.1 mg, yield 15%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography
  7. dissolutionThe purification product was then dissolved in methanol
  8. additionthe solution was added dropwise to water
  9. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ed51d35ca14940f9b484eac0d06710ef
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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