Benzophenone imine → HCID 58710024, compound

HRID 2375897Notes

Reaction equation

HRID 2375897 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[C:15](=[NH:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>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].C1(C)C=CC=CC=1>[C:15](=[N:28][C:2]1[CH:3]=[CH:4][C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 11989077HCID 11989077, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 58710024HCID 58710024, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a dried flask were added 5-bromo-1-phenyl-1H-pyridin-2-one (125 mg, 0.500 mmol), benzophenone imine (100 μl, 0.600 mmol), tris(dibenzylideneacetone)-dipalladium(0) (1.14 mg, 1.25 μmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.33 mg, 3.75 μmol), sodium tert-butoxide (67.2 mg, 0.700 mmol), and toluene (3 ml). The above mixture was flushed with N2 for 5 min and was then heated at 80° C. under an atmosphere of nitrogen for 5 h. After that time, the heating was stopped and the reaction mixture was diluted with ethyl ether (30 ml), filtered and concentrated to obtain light-brown oil, which was then purified by chromatography on silica gel (10 g) eluting with 100 ml of 10%, 20%, 30% and 40%, and 300 ml 50% EtOAc/hexane to obtain the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ=6.45 (d, 1H, J=9.6 Hz), 6.89 (d, 1H, J=2.8 Hz), 7.00 (dd, 1H, J=2.8 & 10.4 Hz), 7.13-7.16 (m, 2H), 7.19-7.22 (m, 2H), 7.33-7.48 (m, 9H), 7.69-7.72 (m, 2H). MS(ES+): m/z 351.05 (100) [MH+]. HPLC: tR=3.46 min (ZQ2000, polar—5 min).

Workup

  1. customThe above mixture was flushed with N2 for 5 min
  2. additionthe reaction mixture was diluted with ethyl ether (30 ml)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain light-brown oil, which
  6. customwas then purified by chromatography on silica gel (10 g)
  7. washeluting with 100 ml of 10%, 20%, 30% and 40%, and 300 ml 50% EtOAc/hexane

Sources & evidence

ORD record
ord-85caa8c43d4c4760a9fce8eaef18fb2b
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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