Cesium carbonate → HCID 11675353, compound

HRID 1894293Notes

Reaction equation

HRID 1894293 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.[F:53][C:54]1[CH:61]=[CH:60][C:57]([CH2:58][OH:59])=[CH:56][CH:55]=1.[CH2:62]([C:69]1[C:73]2[C:74]([Cl:78])=[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:78].[CH2:62]([C:69]1[C:73]2[C:74]([O:59][CH2:58][C:57]3[CH:60]=[CH:61][C:54]([F: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 680224-Fluorobenzylic alcoholHCID 634876Binap, (A+-)-HCID 707004383-Benzyl-4-chloro-2-methyl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 11675353HCID 11675353, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Cesium carbonate (93 mg, 0.28 mmol), (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (12 mg, 0.021 mmol), tris(dibenzylideneacetone)dipalladium(0) (9 mg, 0.010 mmol), and 4-fluorobenzyl alcohol (0.031 ml, 0.28 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 and then recrystallized in n-hexane (5 ml). The resulting solid was dissolved in ethyl ether (2 ml), saturated with hydrochloric acid gas, and then filtered to give the titled compound as a white solid. (Yield: 42.3%)

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. customrecrystallized in n-hexane (5 ml)
  6. dissolutionThe resulting solid was dissolved in ethyl ether (2 ml), saturated with hydrochloric acid gas
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d95b3fc25a534d7a99e0ba1113b47c64
Source dataset
uspto-grants-2013_08
Patent number
US08513277B2

Reaction notes

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