Iodobenzene → HCID 70665410, compound

HRID 333551Notes

Reaction equation

HRID 333551 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2].I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC([O-])(C)C.[Na+]>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].C1(P(C2C=CC=CC=2)C2C=CC=C3C=2C(C2C4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C=CC=2)=CC=C3)C=CC=CC=1>[CH2:1]([NH:3][C:4]1[C:9]([NH:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

7

Reactant 3

HCID 11575IodobenzeneHCID 13451717N~2~-Ethylpyridine-2,3-diamineHCID 23676156Sodium t-butoxide

Product 1

HCID 70665410HCID 70665410, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 99390178,8'-Bis(diphenylphosphino)-1,1'-binaphthaleneCatalystHCID 1140TolueneSolvent

Procedure

N2-ethylpyridine-2,3-diamine (16.00 g, 117 mmol) and iodobenzene (19.61 mL, 175 mmol) were suspended in 300 mL of toluene. 8,8′-Bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) (2.179 g, 3.50 mmol) and Pd2 dba3 (2.136 g, 2.333 mmol) were added, followed by sodium 2-methylpropan-2-olate (16.81 g, 175 mmol). The reaction flask was filled with nitrogen, stirred and refluxed overnight. The reaction mixture was cooled down, filtered through a silica plug and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate 4/1) to provide N2-ethyl-N3-phenylpyridine-2,3-diamine as a brown solid (8.5 g, 34%).

Workup

  1. additionThe reaction flask was filled with nitrogen
  2. temperaturerefluxed overnight
  3. temperatureThe reaction mixture was cooled down
  4. filtrationfiltered through a silica plug
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-26db4b1c2f20484c8746d5a06ff7e0be
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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