Benzophenone imine → HCID 67281784, compound

HRID 2387730Notes

Reaction equation

HRID 2387730 reaction equation
C(=[NH:14])(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].Cl[C:68]1[C:73]([O:74][CH2:75][O:76][CH3:77])=[CH:72][C:71]([F:78])=[CH:70][N:69]=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].C(OCC)C.C1(C)C=CC=CC=1>[F:78][C:71]1[CH:72]=[C:73]([O:74][CH2:75][O:76][CH3:77])[C:68]([NH2:14])=[N:69][CH:70]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthylHCID 86664267HCID 86664267, compound

Product 1

HCID 67281784HCID 67281784, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

Benzophenoneimine (55.3 ul), 2,2-bis(diphenylphosphino)-1,1-binaphthyl (29.3 mg), sodium tert-butoxide (22.6 mg) and Pd2DBA3 (15.3 mg) were added to a toluene (0.5 ml) solution of the compound 319-1 (30 mg). The reaction solution was heated to 100° C. and stirred for 3 hours. Diethyl ether was added to the reaction solution, and the obtained mixture was filtered with Celite. The filtrate was concentrated under reduced pressure. 2 M hydrochloric acid (78.5 ul) was added to a THF (1 ml) solution of the residue, and the obtained mixture was stirred at room temperature for 12 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=9:1 to ethyl acetate), so as to obtain the title compound (17 mg).

Workup

  1. filtrationthe obtained mixture was filtered with Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. addition2 M hydrochloric acid (78.5 ul) was added to a THF (1 ml) solution of the residue
  4. stirringthe obtained mixture was stirred at room temperature for 12 hours
  5. additionA saturated sodium bicarbonate aqueous solution was added to the reaction solution
  6. extractionthe mixture was extracted with dichloromethane
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=9:1 to ethyl acetate)

Sources & evidence

ORD record
ord-2fddb126e2a04dc8a351854a33bc67ed
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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