Cesium carbonate → HCID 67143268, compound

HRID 1932329Notes

Reaction equation

HRID 1932329 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].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.[Cl:53][C:54]1[N:55]=[CH:56][CH:57]=[C:58]2[C:62]([CH3:63])=[C:61]([CH3:64])[N:60]([CH2:65][CH:66]([CH3:68])[CH3:67])[C:59]=12.[CH3:69][C:70]1[CH:77]=[CH:76][C:73]([CH2:74][NH2:75])=[CH:72][CH:71]=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]>[ClH:53].[CH2:65]([N:60]1[C:59]2=[C:54]([NH:75][CH2:74][C:73]3[CH:76]=[CH:77][C:70]([CH3:69])=[CH:71][CH:72]=3)[N:55]=[CH:56][CH:57]=[C:58]2[C:62]([CH3:63])=[C:61]1[CH3:64])[CH:66]([CH3:68])[CH3:67]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 660354-MethylbenzylamineHCID 634876Binap, (A+-)-HCID 117014497-Chloro-1-isobutyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 67143268HCID 67143268, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Cesium carbonate (97 mg, 0.317 mmol) and (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (20 mg, 0.0317 mmol) were added to a solution of 7-chloro-1-isobutyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine (50 mg, 0.211 mmol) prepared in Step 2, tris(dibenzylideneacetone)dipalladium (0) (11 mg, 0.0106 mmol), and 4-methylbenzylamine (40 ml, 0.317 mmol) in anhydrous toluene (1.1 ml). The reaction mixture was refluxed for 40 hours and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=15/85, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 15 mg of the titled compound as a white solid. (Yield: 21%).

Workup

  1. temperatureThe reaction mixture was refluxed for 40 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=15/85
  4. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f4a958833de94609acbdf27368108474
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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