Water → HCID 15479547, compound

HRID 365510Notes

Reaction equation

HRID 365510 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=2)[C:13]([CH3:22])([CH3:21])[CH2:12][C:11]1=[O:23])([CH3:9])[CH3:8].[OH2:24].[CH3:25][CH2:26][O:27][CH2:28][CH3:29]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:7]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:13]3[CH:14]=[CH:15][C:25]([C:26]([O:27][CH2:28][CH3:29])=[O:24])=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)[C:13]([CH3:21])([CH3:22])[CH2:12][C:11]1=[O:23])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 15479546HCID 15479546, compound2×

Product 1

HCID 15479547HCID 15479547, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 1140TolueneSolvent

Procedure

A 25 mL round bottom flask was connected to a reflux condenser and the apparatus flame-dried under high vacuum. The vacuum was broken by the addition of dry argon, and the flask was allowed to cool to room temperature. The flask was charged with 0.295 g (0.90 mmol) of powdered anhydrous cesium carbonate, 12 mg (0.013 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd2 (dba)3), and 12 mg (0.019 mmol) of (S)-(-)-2,2'-bis(diphenylphosphino)1,1'-binaphthyl (BINAP), and the apparatus was evacuated and filled with dry argon 3 times. A solution of (1-isopropyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amine (Compound 1, 0.18 g, 775 mmol) and ethyl 4-iodoobenzoate (0.178 g, 0.65 mmol, available as described in U.S. Pat. No. 5,616,712) in 2 mL of dry toluene was added and the flask was immersed in an oil bath heated to 100° C. After 16 hours, 6 mg of Pd2 (dba)3 and 6 mg of BINAP were added and stirring at 100° C. was continued until the reaction was complete as judged by TLC analysis. The solution was cooled to room temperature and poured into a separatory funnel containing water and ether. The layers were separated and the aqueous layer was extracted 3 times with ether. The combined ether layers were washed once with brine, and dried over magnesium sulfate, and the solvents were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using 10% ethyl acetate in hexanes, and gave the title compound.

Workup

  1. customA 25 mL round bottom flask was connected to a reflux condenser
  2. customthe apparatus flame-dried under high vacuum
  3. additionThe vacuum was broken by the addition of dry argon
  4. customthe apparatus was evacuated
  5. additionfilled with dry argon 3 times
  6. customthe flask was immersed in an oil bath
  7. temperatureheated to 100° C
  8. temperatureThe solution was cooled to room temperature
  9. additionpoured into a separatory funnel
  10. customThe layers were separated
  11. extractionthe aqueous layer was extracted 3 times with ether
  12. washThe combined ether layers were washed once with brine
  13. dry with materialdried over magnesium sulfate
  14. customthe solvents were removed under reduced pressure
  15. customThe residue was purified by flash chromatography on silica gel using 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-125aa371b6284b329b45cf6a61562c39
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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