Tri-o-tolylphosphine → HCID 67047655, compound

HRID 606854

Reaction equation

HRID 606854 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.I[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28].[CH:32]([C:34]1[CH:35]=[N:36][CH:37]=[C:38]([CH:41]=1)[C:39]#[N:40])=[CH2:33]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[C:27]([C:26]1[CH:25]=[C:24]([CH:33]=[CH:32][C:34]2[CH:35]=[N:36][CH:37]=[C:38]([CH:41]=2)[C:39]#[N:40])[CH:31]=[CH:30][CH:29]=1)#[N:28]

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 1443413-IodobenzonitrileHCID 670475755-Vinylnicotinonitrile

Product 1

HCID 67047655HCID 67047655, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Prepare essentially as described in EXAMPLE 15 using palladium(II) acetate (0.009 g, 0.04 mmol), tri-o-tolylphosphine (0.024 g, 0.08 mmol), copper (I) iodide (0.004 g, 0.02 mmol), 3-iodobenzonitrile (0.9 g, 3.93 mmol) and 5-vinylnicotinonitrile, (prepared essentially as described in PREPARATION 51), (0.715 g, 5.5 mmol) at 110° C. for 5 h. Add diethyl ether and wash with water three times. Filter the organic layer and concentrate to give the title compound (0.530g, 59%).

Workup

  1. customPrepare essentially
  2. custom(prepared essentially
  3. customas described in PREPARATION 51), (0.715 g, 5.5 mmol) at 110° C. for 5 h
  4. washAdd diethyl ether and wash with water three times
  5. filtrationFilter the organic layer
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-6f714f42118e4dbdace78609e1ba6866
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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