Benzophenone imine → HCID 59428634, compound

HRID 1515310Notes

Reaction equation

HRID 1515310 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].Br[C:54]1[CH:59]=[CH:58][N:57]=[C:56]2[N:60]([CH2:63][C:64]3[CH:69]=[CH:68][N:67]=[CH:66][CH:65]=3)[CH:61]=[CH:62][C:55]=12.[C:70](=[NH:83])([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=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:77]1([C:70]([C:71]2[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=2)=[N:83][C:54]2[C:55]3[CH:62]=[CH:61][N:60]([CH2:63][C:64]4[CH:69]=[CH:68][N:67]=[CH:66][CH:65]=4)[C:56]=3[N:57]=[CH:58][CH:59]=2)[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 59428624HCID 59428624, compound

Product 1

HCID 59428634HCID 59428634, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A 25-mL round-bottomed flask equipped with magnetic stirrer and reflux condenser is charged with rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.040 g, 0.063 mmol), Pd2dba3 (0.019 g, 0.021 mmol) and sodium tert-butoxide (0.282 g, 2.94 mmol). The reaction vessel is then purged with a stream of nitrogen for 0.5 h. After such time, a solution of Compound 1b (0.600 g, 2.10 mmol) in toluene (6 mL) followed by benzophenone imine (0.45 g, 2.51 mmol) is added. The reaction is then heated at reflux for 2 h. After such time the reaction is cooled to room temperature and concentrated under reduced pressure. The resulting oil is then purified by column chromatography to afford Compound 1c as a yellow oil.

Workup

  1. customA 25-mL round-bottomed flask equipped with magnetic stirrer
  2. temperaturereflux condenser
  3. customThe reaction vessel is then purged with a stream of nitrogen for 0.5 h
  4. additionis added
  5. temperatureThe reaction is then heated
  6. temperatureat reflux for 2 h
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil is then purified by column chromatography

Sources & evidence

ORD record
ord-35aa231a6c704ddd89df2fe4a65334c1
Source dataset
uspto-grants-2012_07
Patent number
US08222421B2

Reaction notes

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