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Trimethylsilylacetylene → 5,5'-Bis(trimethylsilylethynyl)-2,2'-bipyridine

HRID 868768
Notes
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Reaction equation

HRID 868768 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)=[N:12][CH:13]=1>C1COCC1.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.[Cu]I>[CH3:1][Si:2]([C:5]#[C:6][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:16][N:15]=2)=[N:12][CH:13]=1)([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 109031035,5'-DIBROMO-2,2'-BIPYRIDINE

Product 1

HCID 52476625,5'-Bis(trimethylsilylethynyl)-2,2'-bipyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

Under dry nitrogen atmosphere, successively trimethylsilyl-acetylene (619 mg, 6.30 mmol), [Pd(PPh3)2Cl2] (112 mg, 159 μmol), CuI (54.5 mg, 286 μmol) and DIPA (4 ml) were added to a stirred suspension of 3 (500 mg, 1.59 mmol) in 30 ml THF. While the mixture was stirred for 24 hours at room temperature, its color turned black. It was stirred together with activated carbon for 20 minutes and filtered over celite. Then the solvent was removed under reduced pressure, the residue was resuspended in hexane, sonicated for 15 minutes and filtered over celite again yielding an orange solution. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica (eluent: CH2Cl2) to yield 430 mg (1.23 mmol, 78%) of pure 4 as an off-white solid. 1H NMR (CDCl3, 250 MHz): δ=8.71 (s, 2H, bpy-H), 8.33 (d, 2H, JHH=8.3 Hz, bpy-H), 7.85 (d, 2H, JHH=7.8 Hz, bpy-H), 0.27 (s, 18H, Si(CH3)3).

Workup

  1. stirringIt was stirred together with activated carbon for 20 minutes
  2. filtrationfiltered over celite
  3. customThen the solvent was removed under reduced pressure
  4. customsonicated for 15 minutes
  5. filtrationfiltered over celite
  6. customagain yielding an orange solution
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by flash column chromatography on silica (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-794d83753447419ebdc7403eb1fa6c8d
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08968886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes