Benzophenone imine → HCID 125497762, compound

HRID 1502140Notes

Reaction equation

HRID 1502140 reaction equation
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.CC(C)([O-])C.[K+].Br[C:54]1[N:59]=[C:58]([CH2:60][C:61]([O:63][CH3:64])=[O:62])[CH:57]=[CH:56][CH:55]=1.[C:65](=[NH:78])([C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>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]>[CH3:64][O:63][C:61](=[O:62])[CH2:60][C:58]1[CH:57]=[CH:56][CH:55]=[C:54]([N:78]=[C:65]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[N:59]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 71720999Methyl (6-bromopyridin-2-yl)acetate

Product 1

HCID 125497762HCID 125497762, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Pd2(dba)3 (4.0 mg, 0.0040 mmol), BINAP (41 mg, 0.065 mmol), and potassium tert-butoxide (490 mg, 4.35 mmol) in toluene (10 mL) was added methyl (6-bromopyridin-2-yl)acetate (1 g, 4.35 mmol) and benzophenone imine (1.1 mL, 6.52 mmol). The reaction was degassed for 15 minutes and then heated at 100° C. for 15 hours in a sealed tube. The reaction was then cooled to room temperature and concentrated in vacuo. The crude residue was taken up in ethyl acetate (200 mL), filtered over celite, and washed with water. The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified via MPLC (0-100% EtOAc/Hex gradient) to afford title compound. LC/MS (M+H)+ 331.

Workup

  1. customThe reaction was degassed for 15 minutes
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered over celite
  5. washwashed with water
  6. dry with materialThe organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified via MPLC (0-100% EtOAc/Hex gradient)

Sources & evidence

ORD record
ord-d25b2d769b094f12af2b1f738b0114ff
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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