Cesium carbonate → Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate

HRID 1713846Notes

Reaction equation

HRID 1713846 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].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:79](=[NH:92])([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:80]1([C:79](=[N:92][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]3)=[CH:9][CH:8]=2)[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=2)[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 59464250Ethyl [3-(4-{[(trifluoromethyl)sulphonyl]oxy}phenyl)cyclohexyl]acetate

Product 1

HCID 59464258Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetateYield 38%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [3-(4-{[(trifluoromethyl)sulphonyl]oxy}phenyl)cyclohexyl]acetate (322 mg, 0.85 mmol) was stirred in dry THF (8 mL) under a nitrogen atmosphere and caesium carbonate (387 mg, 1.19 mmol), palladium(II) acetate (12 mg, 0.05 mmol) and BINAP (32 mg, 0.05 mmol) were added followed by benzophenone imine (0.214 mL, 1.27 mmol). The reaction vessel was degassed 6 times and stirred under reflux for 16 h. The mixture was extracted with ether (2×100 mL) and washed with water (100 mL). The organic extracts were dried and concentrated by evaporation to give an oil that was purified by chromatography eluting with 0-30% EtOAc/isohexane to give the title compound (137 mg, 38%) as an oil; 1H NMR δ 0.81-2.48 (m, 9H), 1.12-1.21 (m, 3H), 2.58-2.72 (m, 1H), 3.97-4.12 (m, 2H), 6.57-6.65 (m, 1H), 6.94-7.04 (m, 1H), 7.10-7.18 (m, 1H), 7.29-7.36 (m, 1H), 7.37-7.78 (m, 10H); MS m/e MH+ 426.

Workup

  1. customThe reaction vessel was degassed 6 times
  2. temperatureunder reflux for 16 h
  3. extractionThe mixture was extracted with ether (2×100 mL)
  4. washwashed with water (100 mL)
  5. customThe organic extracts were dried
  6. concentrationconcentrated by evaporation
  7. customto give an oil that
  8. customwas purified by chromatography
  9. washeluting with 0-30% EtOAc/isohexane

Sources & evidence

ORD record
ord-0a90d8daa0af45c696388dce9fddc3fe
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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