4-(Trifluoromethoxy)aniline → HCID 11717717, compound

HRID 1437750Notes

Reaction equation

HRID 1437750 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:14])[N:3]=1.CC(C)([O-])C.[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[F:67][C:68]([F:78])([F:77])[O:69][C:70]1[CH:75]=[CH:74][C:73]([NH2:76])=[CH:72][CH:71]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:14][C:4]1[N:3]=[C:2]([NH:76][C:73]2[CH:74]=[CH:75][C:70]([O:69][C:68]([F:67])([F:77])[F:78])=[CH:71][CH:72]=2)[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=1

Participants

8

Reactant 4

HCID 6008484-(Trifluoromethoxy)anilineHCID 634876Binap, (A+-)-HCID 116155784-(2,6-dichloro-pyridin-4-yl)-morpholineHCID 23665647Potassium tert-butoxide

Product 1

HCID 11717717HCID 11717717, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-(2,6-dichloro-pyridin-4-yl)-morpholine (0.500 g, 2.15 mmol) in toluene (6 mL) were added potassium tert-butoxide (0.109 g, 0.973 mmol), palladium(II)acetate (24.13 mg, 0.107 mmol), BINAP (67.0 mg, 0.107 mmol) and 4-trifluoromethoxyphenylamine (456 mg, 2.58 mmol), in a 10 mL reaction vessel. This reaction mixture was subjected the microwave radiation, in which the microwave power was 250 W, to attain a reaction temperature of 150° C. After this reaction proceeded for 30 min, water (200 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel (elution 30:70 ethyl acetate:petroleum ether) to afford the desired compound as a light yellow solid (140 mg, yield 18%).

Workup

  1. customin a 10 mL reaction vessel
  2. customa reaction temperature of 150° C
  3. extractionthe reaction product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe product was purified through column chromatography

Sources & evidence

ORD record
ord-2cef501a499e408d92dc68bb5c9daa9a
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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