Triphenylphosphine → 2-[1-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzonitrile

HRID 1742415Notes

Reaction equation

HRID 1742415 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([C:22]1[NH:32][C:25]2=[N:26][C:27]([CH3:31])=[CH:28][C:29]([CH3:30])=[C:24]2[N:23]=1)[CH3:21].O[CH:34]1[C:42]2[C:37](=[CH:38][C:39]([C:43]3[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=3[C:45]#[N:46])=[CH:40][CH:41]=2)[CH2:36][CH2:35]1>C1(C)C=CC=CC=1>[CH2:20]([C:22]1[N:32]([CH:34]2[C:42]3[C:37](=[CH:38][C:39]([C:43]4[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=4[C:45]#[N:46])=[CH:40][CH:41]=3)[CH2:36][CH2:35]2)[C:25]2=[N:26][C:27]([CH3:31])=[CH:28][C:29]([CH3:30])=[C:24]2[N:23]=1)[CH3:21]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 190089042-(1-Hydroxy-indan-5-yl)-benzonitrileHCID 178437439HCID 178437439, compound

Product 1

HCID 190089182-[1-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of triphenylphosphine (393 mg, 1.5 mmol) in toluene was slowly added diethylazadicarboxylate (261 mg, 1.5 mmol). After 1 hour, this solution was added to a mixture of 2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (350 mg, 2.0 mmol) and 2-(1-hydroxy-indan-5-yl)-benzonitrile (246 mmol, 1.01 mmol). The reaction mixture was stirred for 17 hours at room temperature and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 30% ethyl acetate/hexanes. The residue was dissolved in CHCl3, hexanes were added to precipitate out a white solid. The mixture was filtered and the filtrate was concentrated in vacuo to give a yellow oil which solidified upon standing.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was chromatographed on SiO2
  3. dissolutionThe residue was dissolved in CHCl3
  4. additionhexanes were added
  5. customto precipitate out a white solid
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customto give a yellow oil which

Sources & evidence

ORD record
ord-1d6cd4d7340846bfacb68db255d450d0
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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