Benzenamine, 3-(methylthio)- → HCID 11529322, compound

HRID 1437739Notes

Reaction equation

HRID 1437739 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][S:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.ClCCl.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]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:12]([S:11][CH3:10])[CH:13]=2)[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

8

Reactant 4

HCID 15693Benzenamine, 3-(methylthio)-HCID 812191,3-Bis(diphenylphosphino)propaneHCID 117373932,6-Dichloro-4-iodopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 11529322HCID 11529322, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To 2,6-dichloro-4-iodopyridine (1.3715 g, 5 mmol) dissolved in toluene (30 mL) were added 3-methylthioaniline (0.73 mL, 6 mmol), tris(dibenzylidene-acetone)dipalladium (90.6 mg, 0.1 mmol), 1,3-bis(diphenylphosphino)propane (80.0 mg, 0.2 mmol), and sodium-tert-butoxide (672.1 mg, 7 mmol). The resulting mixture was allowed to stir at reflux for 12-18 hours. The sample was diluted in dichloromethane and filtered through Celite™. The Celite™ was washed with dichloromethane and the filtrate was washed two times with water and one time with brine. The organic phase was dried over potassium carbonate and concentrated by rotary evaporation. The resulting sample (9) was dried for 12-18 hours under vacuum. The sample was used without purification.

Workup

  1. temperatureat reflux for 12-18 hours
  2. filtrationfiltered through Celite™
  3. washThe Celite™ was washed with dichloromethane
  4. washthe filtrate was washed two times with water and one time with brine
  5. dry with materialThe organic phase was dried over potassium carbonate
  6. concentrationconcentrated by rotary evaporation
  7. dry with materialThe resulting sample (9) was dried for 12-18 hours under vacuum
  8. customThe sample was used without purification

Sources & evidence

ORD record
ord-49d992825ad2495da4b2436a5d76dd94
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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