Cesium carbonate → HCID 59458312, compound

HRID 1930333Notes

Reaction equation

HRID 1930333 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[C:19](=[N:32][NH2:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]1([C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:32][NH:33][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79304DiphenylmethylidenehydrazineHCID 152903586-Quinolinyl trifluoromethanesulfonate

Product 1

HCID 59458312HCID 59458312, compoundYield 70.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

To a suspension of quinolin-6-yl trifluoromethanesulfonate (40 g, 0.14 mol), benzophenone hydrazone (35.6 g, 0.18 mol), cesium carbonate (74 g, 0.23 mol) and 1,1′-bis(diphenylphosphino)ferrocene (2.5 g, 4.5 mmol) in degassed toluene (1 L) was added palladium acetate (0.013 g, 0.058 mmol). The resultant mixture was heated to 90° C. under a nitrogen atmosphere. After 16 h, the mixture was concentrated in vacuo and the residue was purified through silica gel column chromatography (20-30% EtOAc in pet ether) to provide 1-(diphenylmethylene)-2-(quinolin-6-yl)hydrazine (32 g, 68.6% yield). 1H-NMR (300 MHz, DMSO-d6): δ 9.22 (s, 1 H), 8.58 (t, J=1.8 Hz, 1 H), 8.13 (d, J=3.6 Hz, 1 H), 7.80 (d, J=3.6 Hz, 1 H), 7.61 (d, J=3.9 Hz, 1 H), 7.59-7.51 (m, 4 H), 7.50 (d, J=3.6 Hz, 2 H), 7.33-7.39 (m, 6H); MS (ESI) m/z: 324 (M+H+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified through silica gel column chromatography (20-30% EtOAc in pet ether)

Sources & evidence

ORD record
ord-98331c5251a84777b05150ade12a29a7
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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