Toluene → HCID 57562594, compound

HRID 1172399Notes

Reaction equation

HRID 1172399 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Cl)[N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:7][C:8]1[N:9]=[C:10]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 21552-AminothiazoleHCID 10796Cesium carbonateHCID 169892,6-Dichloropyridine

Product 1

HCID 57562594HCID 57562594, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.37 g (9.26 mmol) of 2-aminothiazole, 0.74 g (7.39 mmol) of 2,6-dichloropyridine, 387 mg (0.621 mmol) of (S)-(−)-2,2′-(bisdiphenylphosphino)-1,1′-binaphthyl, 322 mg (0.311 mmol) of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 2.77 g (8.50 mmol) of cesium carbonate and 10 ml of toluene was heated under reflux for 1 hour and 30 minutes, cooled to room temperature and diluted with ethyl acetate. An insoluble matter was filtered off using Celite and the resulting ethyl acetate solution was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography to give 990 mg (4.68 mmol) of the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour and 30 minutes
  3. filtrationAn insoluble matter was filtered off
  4. washthe resulting ethyl acetate solution was washed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-664342d1e05f4d81b4b4c4503b0c2144
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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