Cesium carbonate → (4-Chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amine

HRID 229014Notes

Reaction equation

HRID 229014 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(O[C:53]1[CH:62]=[C:61]2[C:56]([C:57]([Cl:63])=[CH:58][CH:59]=[N:60]2)=[CH:55][C:54]=1[O:64][CH3:65])(=O)=O.[N:68]1([CH2:74][CH2:75][NH2:76])[CH2:73][CH2:72][O:71][CH2:70][CH2:69]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:63][C:57]1[C:56]2[C:61](=[CH:62][C:53]([NH:76][CH2:75][CH2:74][N:68]3[CH2:73][CH2:72][O:71][CH2:70][CH2:69]3)=[C:54]([O:64][CH3:65])[CH:55]=2)[N:60]=[CH:59][CH:58]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 4082852-MorpholinoethylamineHCID 634876Binap, (A+-)-HCID 859455444-Chloro-6-methoxy-quinolin-7-yl trifluoro-methanesulfonate

Product 1

HCID 23078325(4-Chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amineYield 14%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Palladium acetate (62 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (170 mg) were dissolved in toluene (16 ml) to prepare a solution which was then stirred at room temperature for 5 min. 4-Chloro-6-methoxy-quinolin-7-yl trifluoro-methanesulfonate (400 mg) and 2-morpholin-4-yl-ethylamine (1.12 ml) were added thereto, and the mixture was further stirred at room temperature for 5 min. Cesium carbonate (1.97 g) was added to the reaction solution, and the mixture was stirred at 90° C. overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform 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 thin layer chromatography using methanol chloroform to give (4-chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amine (53 mg, yield 14%).

Workup

  1. customto prepare a solution which
  2. stirringthe mixture was further stirred at room temperature for 5 min
  3. stirringthe mixture was stirred at 90° C. overnight
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was then washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-40c192cf71c941748fa0d57933c990fb
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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