2-Iodobenzonitrile → 2-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrile

HRID 1886070Notes

Reaction equation

HRID 1886070 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Sn](CCCC)(CCCC)CCCC)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[C:32]#[N:33]>C1COCC1.CCOCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:30]2[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=2[C:32]#[N:33])=[N:14][CH:15]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 27593582-IodobenzonitrileHCID 11756135[5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannane

Product 1

HCID 99963952-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrileYield 68.6%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannane (11.5 g, 0.022 mol), 2-iodobenzonitrile (5.1 g, 0.022 mol), CuI (0.43 g, 0.002 mol), and bis(triphenylphosphine)palladium(II) chloride (0.80 g, 0.001 mol) in THF (40 mL) was heated under reflux for 48 h. The mixture was diluted with ether and washed with saturated aqueous NH4Cl, aqueous NH4OH, water, and brine, dried (MgSO4), and concentrated to give 4.9 g (67%) of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. washwashed with saturated aqueous NH4Cl, aqueous NH4OH, water, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-495245b23c6441b5bc8a6b7d2ddf0078
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

Loading…