Benzophenone imine → HCID 131734295, compound

HRID 1502143Notes

Reaction equation

HRID 1502143 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[CH:59]=[C:58]([CH2:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH:57]=[CH:56][N:55]=1.[C:68](=[NH:81])([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=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]>[C:64]([O:63][C:61](=[O:62])[CH2:60][C:58]1[CH:57]=[CH:56][N:55]=[C:54]([N:81]=[C:68]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[CH:59]=1)([CH3:67])([CH3:66])[CH3:65]

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 772315131,1-Dimethylethyl 2-bromo-4-pyridineacetate

Product 1

HCID 131734295HCID 131734295, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Pd2(dba)3 (1.9 mg, 0.0001 mmol), BINAP (5 mg, 0.008 mmol), and potassium tert-butoxide (62 mg, 0.55 mmol) in toluene (3 mL) was added tert-butyl (2-bromopyridin-4-yl)acetate (150 mg, 0.55 mmol) and benzophenone imine (140 μL, 0.83 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 ambient temperature and concentrated in vacuo. The crude residue was dissolved 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)+373.

Workup

  1. customThe reaction was degassed for 15 minutes
  2. temperatureThe reaction was then cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude residue was dissolved ethyl acetate (200 mL)
  5. filtrationfiltered over celite
  6. washwashed with water
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified via MPLC (0-100% EtOAc/Hex gradient)

Sources & evidence

ORD record
ord-903a7309130143afbad227f5c2d77b2c
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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