Benzophenone imine → HCID 86760778, compound

HRID 2374152Notes

Reaction equation

HRID 2374152 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[CH3:8].CC([O-])(C)C.[Na+].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.[C:63](=[NH:76])([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=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]>[CH3:10][O:9][C:6]1[C:7]([CH3:8])=[C:2]([N:76]=[C:63]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:3]=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 573637893-Bromo-5-methoxy-4-methylpyridine

Product 1

HCID 86760778HCID 86760778, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

3-Bromo-5-methoxy-4-methylpridine (0.76 g) was placed in a single neck round bottom flask with NaOtBu (1.4 eq), BINAP (0.8 eq), Pd2(dba)3 (0.25 eq), and benzhydrylideneamine (1 eq) in toluene 20 ml, and refluxed at 150° C. for 4 h. The reaction was partitioned between water and EtOAc, and the EtOAc layer dried over Na2SO4. The product was purified by SGC (EtOAc/ Hexane) affording 5-methoxy-4-methyl-N-(diphenymethylene)pyridine-3-amine. MS (ESI+) for m/z 302 [M+H]+.

Workup

  1. customThe reaction was partitioned between water and EtOAc
  2. dry with materialthe EtOAc layer dried over Na2SO4
  3. customThe product was purified by SGC (EtOAc/ Hexane)

Sources & evidence

ORD record
ord-4d6151c4ff2f4f8497c04453ce07e5fa
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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