Triethylamine → HCID 86648161, compound

HRID 449859Notes

Reaction equation

HRID 449859 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C.Br[C:57]1[CH:58]=[C:59]2[C:64](=[CH:65][CH:66]=1)[N:63]=[C:62]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[CH:61]=[CH:60]2.[C:73](=[NH:86])([C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:80]1([C:73]([C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=2)=[N:86][C:57]2[CH:58]=[C:59]3[C:64](=[CH:65][CH:66]=2)[N:63]=[C:62]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH:61]=[CH:60]3)[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 534383316-Bromo-2-phenylquinoline

Product 1

HCID 86648161HCID 86648161, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

In a 20 mL microwave tube was charged cesium carbonate (0.440 mL, 5.50 mmol), palladium(II)acetate (0.018 g, 0.079 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.068 g, 0.118 mmol) in dioxane (6.0 mL) to give a yellow suspension. The mixture was stirred for 10 minutes and then triethylamine (0.016 mL, 0.118 mmol) was added. The solution was stirred for another 10 minutes; and then 6-bromo-2-phenylquinoline (1.1168 g, 3.93 mmol) and benzophenone imine (0.791 mL, 4.72 mmol) were added as a solution in dioxane (6.0 mL). The mixture was heated at 100° C. overnight. The mixture was cooled to room temperature and dilute with ethyl acetate. The organics were washed 2×100 mL with water, dried over magnesium sulfate, filtered, and concentrated onto silica gel. The reaction was purified by flash chromatography using an Argonaut Flashmaster Solo, 20 g column (10% ethyl acetate:hexanes for 30 min) to afford a yellow oil. (ESI(+)) m/e 385.0 (M+H)+.

Workup

  1. customto give a yellow suspension
  2. stirringThe solution was stirred for another 10 minutes
  3. temperatureThe mixture was cooled to room temperature
  4. washThe organics were washed 2×100 mL with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated onto silica gel
  8. customThe reaction was purified by flash chromatography
  9. customan Argonaut Flashmaster Solo, 20 g column (10% ethyl acetate:hexanes for 30 min)
  10. customto afford a yellow oil

Sources & evidence

ORD record
ord-e4d950b0204246fb9e1a70e4bcda710e
Source dataset
uspto-grants-2013_07
Patent number
US08486933B2

Reaction notes

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