Cesium carbonate → HCID 11553042, compound

HRID 1894290Notes

Reaction equation

HRID 1894290 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[CH:61]=[CH:60][C:57]([CH2:58][NH2:59])=[CH:56][CH:55]=1.[CH2:62]([C:69]1[C:73]2[C:74](Cl)=[N:75][CH:76]=[CH:77][C:72]=2[NH:71][C:70]=1[CH3:79])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=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].[CH2:62]([C:69]1[C:73]2[C:74]([NH:59][CH2:58][C:57]3[CH:60]=[CH:61][C:54]([Cl:53])=[CH:55][CH:56]=3)=[N:75][CH:76]=[CH:77][C:72]=2[NH:71][C:70]=1[CH3:79])[C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 660364-ChlorobenzylamineHCID 634876Binap, (A+-)-HCID 707004383-Benzyl-4-chloro-2-methyl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 11553042HCID 11553042, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Cesium carbonate (85 mg, 0.26 mmol), (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (11 mg, 0.020 mmol), tris(dibenzylideneacetone)dipalladium(0) (8 mg, 0.009 mmol), and 4-chlorobenzylamine (0.032 ml, 0.26 mmol) were added to a solution of 3-benzyl-4-chloro-2-methyl-1H-pyrrolo[3,2-c]pyridine (50 mg, 0.17 mmol) prepared in Preparation 2 in toluene (3 ml). The reaction mixture was refluxed under stirring for 2 days. The reaction mixture was cooled to room temperature, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography, dissolved in ethyl ether (2 ml), and then saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a white solid. (Yield: 42.2%)

Workup

  1. temperatureThe reaction mixture was refluxed
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography
  5. dissolutiondissolved in ethyl ether (2 ml)
  6. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-52538fc3e80244e2803f1be32ffb60f2
Source dataset
uspto-grants-2013_08
Patent number
US08513277B2

Reaction notes

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