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

HRID 2176471
Notes
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Reaction equation

HRID 2176471 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 mol), CuI (54.5 mg, 286 mol) 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-3705dc103ccc4e03a2051e4952e14356
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067181B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes