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

HRID 556140
Notes
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Reaction equation

HRID 556140 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][N:9]=2)=[N:6][CH:7]=1.N([CH:19]([CH3:21])C)C(C)C.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24]>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.C1COCC1>[CH3:22][Si:23]([C:26]#[C:27][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:21]#[C:19][Si:23]([CH3:25])([CH3:24])[CH3:22])=[CH:10][N:9]=2)=[N:6][CH:7]=1)([CH3:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 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)Catalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

Firstly, a mixture of 5,5′-dibromo-2,2′-bipyridyl (300 mg, 0.96 mmol), PdCl2(PPh3)2 (60 mg, 0.085 mmol) and CuI (30 mg, 0.16 mmol) was added with dist. THF (18 mL), dist. i-Pr2NH (2.4 mL) and trimethylsilylacetylene (467 μL, 3.3 mmol). The resultant mixture was then stirred under a nitrogen atmosphere at room temperature for 29 hours to obtain a reaction mixture. Subsequently, a salt contained in the reaction mixture was removed through a celite filtration process. The organic layer thus obtained was concentrated to obtain a crude product (I) Then, the obtained crude product (I) was separated and purified by silica gel column chromatography (CH2Cl2=100) to obtain 5,5′-bis(trimethylsilylethynyl)-2,2′-bipyridyl.

Workup

  1. additionwas added with dist
  2. customto obtain a reaction mixture
  3. customwas removed through a celite filtration process
  4. customThe organic layer thus obtained
  5. concentrationwas concentrated
  6. customto obtain a crude product (I)
  7. customthe obtained crude product (I)
  8. customwas separated
  9. custompurified by silica gel column chromatography (CH2Cl2=100)

Sources & evidence

ORD record
ord-74b63bfd3d7045f9a49e092faedae426
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053588B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes