p-Aminoacetophenone → HCID 11572724, compound

HRID 1437744Notes

Reaction equation

HRID 1437744 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)=[O:12].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.C(Cl)Cl.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].C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([C:11](=[O:12])[CH3:10])=[CH:14][CH:15]=2)[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

9

Reactant 4

HCID 7468p-AminoacetophenoneHCID 812191,3-Bis(diphenylphosphino)propaneHCID 117373932,6-Dichloro-4-iodopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 11572724HCID 11572724, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2,6-dichloro-4-iodopyridine (0.8177 g, 3 mmol) and 4-aminoacetophenone (0.4891 g, 3.6 mmol) dissolved in dry toluene (10 mL) and THF (2 mL) was added tris(dibenzylideneacetone)dipalladium(0) (0.0571 g, 0.06 mmol), 1,3-bis(diphenyl-phospino)propane (0.0499 g, 0.12 mmol), and sodium-tert-butoxide (0.4042 g, 4.2 mmol). The reaction mixture was stirred and refluxed for 12 to 14 hours under N2. The reaction mixture was diluted with CH2Cl2 and filtered through Celite™, then rinsed with CH2Cl2. The filtrate was washed two times with water and one time with brine. The organic phase was collected and dried over potassium carbonate. The filtered sample was concentrated, and the resulting solid was dried for 12-18 hours under vacuum.

Workup

  1. temperaturerefluxed for 12 to 14 hours under N2
  2. filtrationfiltered through Celite™
  3. washrinsed with CH2Cl2
  4. washThe filtrate was washed two times with water and one time with brine
  5. customThe organic phase was collected
  6. dry with materialdried over potassium carbonate
  7. concentrationThe filtered sample was concentrated
  8. customthe resulting solid was dried for 12-18 hours under vacuum

Sources & evidence

ORD record
ord-33bd660ad50f493295d2bad1d61534bf
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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